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2,411,662
Patented Nov. 26, 1946‘
UNITED STATES PATENT OFFICE
2,411,662
IMINO-DI-FATTY ACID AMIDE
Henry Martin and Hans Gysin, Basel, Switzer
land, assignors to the firm J. R. Geigy A. G.,
'
.
Basel, Switzerland
No Drawing. Ap lication April 28, 1944, Serial
No. 533,265. 11 Switzerland May 13, 1943
(Cl. 260-561)
9 Claims.
1
,
chloracetic acid,
chloracetic ester,
Heterocyclic and aromatic carboxylic acid
amides have already been ~described as being
agents, acting in a promoting manner, while
, chloracetonitrile,
chloracetic acid diethyl amide,
corresponding compounds of the aliphatic series
chloracetic acid diallylamide,
often show an opposite e?icacy. Thus for ex
ample the isovalerianic acid diethyl amide (of.
Deutsche med. Wochenschrift 1901, No. 49) as
'
a-bromopropionic acid piperidide,
a-bromopropionic acid ethyl ester,
a-bI‘OmODI‘ODiOIIIC acid diethyl amide,
well as the methyl ethyl acetic acid diethyl
a-bromopropionic acid methyl ethyl amide,
amide (cf. Archiv der Pharmazie 1935, 202) pro10 a-bromopropionic acid methyl anilide,
vokes a sedative’action.
a-bromopropionic acid monoethyl amide,
It has now surprisingly been found thatv N
ya-bromobutyric acid ethyl ester,‘
substituted imino-di-fatty acid amide containing
a-bl'OIIlOblltYl‘iC acid ethyl amide,
at least a double substituted amide group pos
a-bromobutyric acid dimethyl amide,
sess valuable therapeutical properties. Such
compounds may be prepared according to vari 15 a-bromobutyric acid methyl ethyl amide,
a-bromotutyric acid diethyl amide,
ous methods, thus for instance in dependence of
a-bromobutyric acid diallyl amide,
the order of succession of the substitution of the
a-bromovalerianic acid dimethyl amide,
imino-N-atom and of the amination.
a-bromovalerianic acid diethyl amide and the
For instance the said compounds may readily
like.
.
be prepared by interaction of N-monosubstituted 20
or N-unsubstituted e-amino fatty acid amides,
A further manner suitable for the production
whose acid amide groups are twice substituted,
of a subgroup of the claimed compounds of sym
with halogen fatty acid derivatives. The N-un—
metrical structure consists in that a-h‘alogen
substituted or N-monosubstituted u-amino fatty
fatty acid amides, the amide nitrogen of which
acid amides required for the interaction and 25 is twice substituted, are brought to double inter
whose acid'amide groups are twice substituted
action by means of ammonia or primary amines.
may be produced by causing a-halogen carboxylic
Moreover, it is also possible to subsequently '
acid amides to react with ammonia or primary
substitute, for instance to alkylate or to cyclo
amines like methyl amine, ethyl amine, propyl
alkylate N-substituted imino-di-fatty acid
amine, butyl amine, amyl amine, hexyl amine, 30 amides, whose amide groups still possess a re
allyl amine, isopropyl amine, cyclohexyl amine,
placeable hydrogen atom (see Titherley, J. Chem.
benzyl amine, phenyl ethyl amine, phenyl iso
Soc. London 79,391, (1901). Furthermore, as far
propyl amine and so on.
The u-halogen car
_ as a hydrogen atom is still present in the imino
boxylic acid amides are prepared according to
group of the imino-di-fatty acid amide, the said
known methods from the corresponding acids 35 hydrogen atom can subsequently be replaced, for
or functional derivatives thereof with secondary
instance by means of alkylating or aralkylating
amines such as dimethyl amine, diethyl amine,
diallyl amine, methyl ethyl amine, methyl
agents like for example dimethyl sulfate, diethyl
sulfate, benzyl chloride, phenyl ethyl bromide or
by any ‘other substitution agents like methyl
propyl amine, methyl aniline, methyl benzyl
amine etc. As examples of a-amino fatty acid 40 iodide or, e. g., by a treatment with formaldehyde
amides which may be used, there may be/enu
and formic acid.
merated:
(
Finally a further preparation method of the
claimed compounds consists in aminating imino
a-methyl amino aceticacid diethyl amide, \
di-fatty acids with one or two free carboxylic
m-methyl amino aceticgacid dimethyl amide,
e-methyl amino propionic acid dimethyl amide, 45 groups or their functional derivatives, for ex
ample by interaction with secondary amines;
u-methyl amino propionic acid diethyl amide,
likewise the salts of the imino-di-fatty acids or
a-ethyl amino propionic acid piperidide,
of mcnobasic derivatives may be caused to react
u-butyl amino propionic acid dimethyl amide,
with carbamic acid‘halides deriving from sec
m-methyl amino‘ butyric acid dimethyl amide,‘
50 ondary amines.
a-ethyl amino butyric acid diethyl amide,
a-ethyl amino butyric acid morpholide,
.
e-methyl amino capronic acid dimethyl amide,
etc.
'
'
-
‘
The new compounds are partly water-soluble; ,
_
a-methyl amino valerianic acid dimethyl amide,
a-methyl amino valerianic acid diethyl amide,
\
by acids they may be transformed into neutral
salts. These substances may be used as therea
, peutics and especially as analeptics; many of
them are also suitable as solvents.
For the interaction of these m-amino fatty acid
amides with halogen fatty acid derivatives c-,
but also other halogen fatty acid derivatives are
especially suitable.
In this connection, there 60'
may be mentioned/for. example:
,
The following examples and tables will illus
trate the invention, without being limited there
to. The parts are by weight.
EXAMPLE 1
37.2 parts of 'a-ethyl amino butyric acid diethyl
2,411,662
4
yields, by means of acids, neutral salts. The
same compound is also obtained by interaction
of ethyl amino acetic acid diethyl amide with
a~halogenbutyric acid diethyl amides.
amide are caused to drop thereinto and the whole 5
Very similar products are obtained by start
is boiled overnight under re?ux. After cooling
ing from a-benzyl amino butyric acid diethyl
the a-ethyl amino butyric acid diethyl amide
amide or ethyl amino isobutyric acid diethyl
hydrochloride separates out; the anisol solution
amide.
is separated from the hydrochloride, made acid
The following Table 1 contains further com
to Congo red by means of hydrochloric acid and 10 pounds of the general formula
freed from the organic solvent. Then the hydroR
amide (prepared from a-bromobutyric acid di
ethyl amide and ethyl amine) are dissolved in
200 parts of anisol and heated to boiling. Then
under stirring 15 parts of chloracetic acid diethyl
chloric acid solution is saturated with potassium
/ '
hydroxide and the N-ethyl imlno butyric acid
(‘mi-CON
acetic acid bis-diethyl amide is dissolved in xylRFN
B2
ene. After distillation of the solvent the prod-‘- 15
II‘
>
not is recti?ed in high vacuo. Its boiling point
at 0.3 mm. pressure is 152°-153° C. The product
which compounds can be prepared according to
is miscible with water and organic Solvents and
the above mentioned two methods.
Table 1
N0.
R|=R|
Ro
R
B. P., mm.
I
1 ...... .-
-CH1 ____ ..
-CH¢CH¢CH:CH3 __________ ..
2 ........... __do._----_
__.--do ..... .-
Y
CH;GHzCH.CON(CH3)1 .................. __
7
143°-14s°c.,0.1-_-_.
I
411110113 ____________________ -_
Form
Liquid;
'
CHCICH2CH.CON(C2H5)1 ................. -_
1a2°-1a5°c.,0.12._._
Do.
-cH,-cH=cH, _________________ __do ....................................... _.
142°-144° 0., 0.02.-..
Do.
‘
.l
4 ...... -. -C,HS__._.. —CHqCH1CH1CHz __________ -_
.
_
CHsCH.CON(C7H5)z ...................... ..
15a°-154° 0., 0.04",‘
Do.
5 __________ --d0 ..... _.
-—CHzCHzCH3 _______________ _.
CHaCHzéHXlONUJzHs): ................. _-
143°—145°C.,0.05.___
D0.
0 ........... .-do _____ ._
—-CH1CH3 ____________________ ._
-cH,.c0N(c,H§), ........................ ..
152°~153° 0., 0.3.-...
Do.
7 .......... “do _____ .-
-CHgCH=CH1 .............. .-
cmomcilcomcmm ................. ..
142=-144° 0., (0.09).-
Do.
I
I
8--___--._..__do ..... ..
-cH,cH,cH,cH: ____
.... ._
'
cmcmoircomcmm ................. ..
14s°-151°G.,0.12....
Do.
157°~160°C.,0.2._.'_-
Do.
1as°-1as° o..o.o4-.-.
Do.
156°—159°C.,0.06..-.
Do.
I
9 .......... _-do ..... __
—CHzCH3_-__'. ............... ._
CH3CH2CHgCH.CON(C2H5)z ............ ._
CH]
1o .......... ._do__-_.-. __._.do _________________________ ..
‘
(an-(211.0orucznmnT ............. ._
CH3
11 .......... __do__-.-.______do _________________________ ..
I
cm'cmcmomcrrcomega», ........ ._
-
I
12--....-...-.do ......... _-do ........................ ..
cmcmcncomomn .................. ..
145°-147°c.,0.2...-.
p0.
13 .......... .410 .......... --do ......................... ..
I
cmcmcmcrrcomcm), ............. -.
l35°-136°C.,0.02--..
Do,
i4 .......... __do ..... __
cnscmcncomomn .................. _.
14s°-151°0.,0.08._..
D0.
CHz—CHzCHzCH3 __________ -.
v
l5 .......... .410 ..... -_
p
——CH¢CH; ____________________ __
I
_
cnacmcmomcncomcnm ......... __
1
1a7°-19o°0.,1.1_....
Do.
147°~150° C.,0.04-_..
D0.
161°~164° 0., 0.03---.
Do.
I
16 .......... ,_dO__.__._ —CH:4CHaCH:CHz .......... __
CH3CHzCH:CHzCH.CON(CHa)z ........ -_
l7 .......... __do__.___. —CH;OH3 ____________________ __
cmcmcrrcoN
!
full-0H,0H,
GHQ-Cg:
_
l
m
_.
do
.....do
.... -.
CH:
I
CH3CH1CH.CON—<
1
19 .......... __do _____ .. -0H2oH2-<
______ -_
'
> ........... _. 1a9°-142° Co.,0.02___
Do.
v
omortcomcmm ...................... ._ 21s°-221° 0., 0.01--. Viscous.
GHQ-CH5
2o __________ __do _____ __
-OH
cm
“man
21.-.-.-.-____do____.--
-C1H5 ________________________ __
GET-CH;
........ __
l68°—17l°0.,0.02----
Liquid.
CH3CH2CH.CONHC2HE .................. ..
153° 0., 0.08 ....... _.
Viscous.
I
/CH2"'CH¢
.-..-d0 ..... .. -cg
0H,; ........ -. —CH¢.CON(C:H;)= ........................ .. 175°-171°c.,o.2.-.__
GET-CH2
23
an
-c.m
_
____ __ —CHg.CONHCzHr ........................ ._
D0.
.
154°—156°C.,0.15-.__
Liquid.
2,411,6_62
5
6
Emma: 2
ethyl dlmethyl amide boils at 143°~145° C. at a
43.2 parts of a-ethyl amino propionic ‘acid di
methyl amide (prepared from a-bromopropionic
acid dlmethyl amide and ethyl amine) are dis
which is easily soluble in water and organic s01
solved in 150 parts of anisol, then at 150“ C. 31.2 5
' parts of a-bromoproplonic acid diethyl amide in
pressure of 0.25 mm. It is an almost colorless‘ oil
vents and which gives neutral salts with acids. ,
The following Table 2 contains'turther com
pounds of the general formula‘
.
50 parts of anisol are caused to drop thereinto
'
and the mixture is boiled under re?ux during 12
cmcmcon
hours. The working up and puri?cation is car- 10
ried out in the manner described in Example 1.
~
/R‘
R
'
|
R,
h
,
The resulting N-ethyl-imino-dipropionic acid di
Table 2
No.
Rl-Rl
Re
R
'
1
r
.
'
2
do
-cH—_cH=0H,.-
4
a
--.do_..-.
omcmcomcng, ....................... .. ’130°-132°C.,
--...do
_____________________
135°-1s7°0.,0.2.---.
Do.
l39°-140° 0., o.a_-.'._
Do.
cmdmcomcim), ______________________ -- 142°-14_4°c.,o.2.._-_
Do.
cmclzmcomomn ...................... -- 132?—135° 0., 0.09..--
Do.
_ _ . "an
an
a ...... .. -—CH: .... -- -0H,cmcH,cH=._Q ........ -01H;
7
do
‘
-c\
7
an
CH3
s.......... --do .... .-
168°-171° 0., 0.85__-_
D0.
133°~136° 0., 0.09;---
Do._
I
-CHzOHzCH1CH: .......... -.
cmcncommm), ...................... -.
I
o _____ __ -c,m..--.. —CH: ........................ _10 .......... -_do ..... -. -cH,cm
_
Liquid.
1as°~1as° 0.,o.a.-_.. [D0,
v-cmcmcm"; ................ ._do _______________
-c,H, ......... .-do _ _ _ _ _
Form
I
—CH; .... -. -cmcm ............
3 ___________ __do ..... _.
B. P., mm.
-
‘
cmcmcomcnm‘
‘133° 0,001
Do.
do
130°-131° 0., 0201.-..
Do.
...__dn
' 147~-15o° 0., 0.32..--
Do.
cmc?oomcmm ...................... -- 153°-160°C.,0.25._.-
Do.
CH:
i1..--._--....do ..... -- 41%
OH:
I
12 ......... --do ..... .- —cH,cH,cmcH,--.'.--_.-.-.--
(lJHa
13.1.. ...... .-do ..... .- —CH;CH; .................... -- cmcmconm ................ .. 14s°-14e° 0., 0.03..-- - Do.
_
14
-'
.....do
do
CHr-CH:
cmcmcoN
CH: ............ _- 160°-162°C.,0.05-_...
CHI-C
Do.
I
Clix-CH:
is
an
an
cmcncoN
,
cH=-_..'_-..' ..... .. 152°-155°C.,0.015___’
cH—c?1
Do.
'
H:
.
pm
...._An
CHI-CHI
..-_.dn
cm H.CON
o ............... -. 15o=_151° 0., 0.02.---
CHPCé:
11.......... __do ..... -_ ——CH:CH|—© ....
'
1s ....... _'..--do.--..-_
—cH_»cH= .................... .-
Do.
I
cmcmcommnm ......... ........... -- 191°-2oo°c.o.o4.--_. Viscous.
I
-
.
CH:CH.CONH.C,H§ ............
....... --
170°-173°0.,0.4.--.-
Liquid.
19 _____ _- -cm ......... -110 ................. _.'. ..... _-
cnlcmomcmcomcnm........
127°-1'29°C.,0.02.._-
Do.
20
.....dn
cngcmcmcmcmcomcm), ......... -_ 15s°—160°0.,0.s..___
Do.
an
cmcnlcmcacomcm), ............. -. 163°-166° c.,o.55--..
Do.
22 ..... ._ —cm .... -. -—CH:.CH; ................... _.
cmcmcmcmcoN(c,H.),._.> ......... .-
131°-133° 0., 0.02-.-.
Do.
23 .......... "do .... .- —CH1CHa .................... _.
CHzCH?HgCHgéECQN(G;H;);.; ...... _. 14o°-143°0.,o.o2-.>._
Do;
-.-dn
21-.-.-. —cm-
I
24 ..... ._ ~—C1H| .... __
-cm ........................ --
25
-cH,cFr-
is1°-1a9°c.,o.os.__.
Do.
use-149° 0., one-.-
Do.
26........--..do .... .- —CH: ........................ .. cmcmcmcmcomcimb-......---..-. 13s=-1a9°c.,o.os.;-.
Do.
do
' '
cmcmcmcmcmcomcmn ........ ..
.-..-dn
2,411,662 '
Table 2-Contlnued
No.
Ru=Ra
Rn
21 _____ .. 421m .... ._
R
B. P., mm.
Form
-01H§. ....................... --
omcmcmémoomcmm ............. ._
141°-143°o.,o.oa..-.
Liquid
2s .......... -410 .......... --do ......................... --
cmcmomomémcommm), ........ ._
1as°-141°o.,o.o2__.-
Do.
29
CE:CH—(]7H.CON(C;H;)g ................ __
1a4°-1a7°o.,o.o2....
Do.
on
...__do
0
1
EXAMPLE 3
The compounds mentioned in the Examples 2
and 3 and in the tables belonging thereto can be
55.8 parts of a-ethyl amino butyric acid diethyl
amide (made from a-bromobutyric acid diethyl 15 produced, as has been described in Example 1,
according to both the cited methods.
amide and ethyl amine) are dissolved in 150
parts of tetraline, then under stirring at 180°
EXAMPLE 4
190° C. 31.2 parts of a-bl‘OIIlODI‘OIJiOHiC acid di
149.5
parts
of
chloracetic
acid diethyl amide
ethyl amide are caused to drop thereinto, where
upon the mixture is maintained for 12 hours at 20 are dissolved in 200 parts of benzene and heated
for 3 hours in the autoclave to 110°—120° C. with
this temperature. The working up takes place=
90 parts of ethyl amine. The ethyl amine hydro
as described in Example 1. The N-ethyl-imino
chloride thus formed is ?ltered by suction, the
butyric acid propionic acid bis-diethyl amide
benzene solution washed with caustic potash lye,
boils at a pressure of 0.2 mm. at 145-l47° C. It
25 freed from the solvent and distilled.
forms with acids easily soluble, neutral salts.
The ?rst running consists of ethyl amino acetic
In the following Table 3 further compounds
'acid diethyl amide; boiling point at 20 mm. pres
of the general formula
sure=1l3°~115° C. The N-ethyl-imino-dieacetic
CHaCH?lJELCON/
Ro—N
acid bis-diethyl amide distills at 0.4 mm. pressure
30 at 158°-159° C. and constitutes a colorless liquid
being easily soluble in water and organic solvents
and producing neutral salts by means of acids.
R2
are enumerated.
The N-ethyl-imino-di-acetic acid bis-diethyl
Table 3
N0.
R1
R1
R0
1_-_-.
—CH; __________ __
-—CH; __________ __
~CH¢CH3 ____ ___ .... -.
I R
B. P., mm. ‘
‘
2 ________ __d0 ________________ __do ___________ __ —CHzCHzCH2CHz__
Form
l
CHZCH-CON(CHS)(C3H7) .... ..
142°—145°C.,0.45____
Liquid.
CHaJJH-CON(CH:):--; ....... .. 127°—130° 0., 0.04.-..
Do.
I
a ________ __do ________________ __do ___________ --
—OH; ______________ -_
4 ........ "do
-c»m
_____do
CHsOH.CON(CzHs)z .......... .-
--.-.dc
‘
142°-145° 0., 0.21m-
D0.
130°—l32° 0., c.1s.___
Do.
5_____ —c,H, .......... __ -o,11, __________ _-
—CHa .............. --
CHaéEECONwHm .......... _.
139°-140° 0.,o.2-____
Do.
a ________ __do ________________ __do ___________
——CH2CH= __________ --
CH3éH-CON(CH3)(C1H7)_-_.._-
144°-146°0.,0.25____
D0.
CHaJJH‘CON(CzHa): __________ --
129°~132° 0., 0.02----
Do.
130°—l33° 0., 0.05----
Do,
7.____ —CH; ............... -410 ___________ -. —CH3 ______________ -_
a ________ __do ________________ __do ........... -. —-CHzCH1
----.do
9_____ —C1H5 _______________ __do ___________ .. -—CHzCH2C£zCHa-.
CHaéH-CDNKCHD: .......... -_ 141°—144°C.,0.1_____
‘
10__'_______do ________________ __do ___________ __
~0H3-.i ........... -_
Do
.
CH3CH-CQN(CIH5)1 __________ __
14a°-14c°o..o.15____
Do.
11____ _____do ________________ __do ___________ __ —-CHzCHzCH¢CH3_- ---__do ........................... __
145°-14s° 0., 0.18..-.
Do.
115°-117°C.,o.03_.__
Do.
I
12----
-cm __________ _-
—CH3 __________ -_
-CH2CH_1._____ _____ __
13_________do ________________ __do ........... --
—C}I3 .............. _-
—CH2CFI~
-__-_do
15_i___ _C,m
__C,m
_-c7m
~
cHacHzcHcoNgcmn ...... __
,
14---- ____-dn
'
‘
I
CH3CH2CH-CON(C2H§)2 _____ __
1ss°-141°0.,o.25..._
Do.
123°—126" 0., 0.02."
Do.
_‘__-_do ........................... ._ 1a5°~1a7°0.,0.03....
Do.
......... .. CHaéH-C0N(C2Hs)z .......... _. 125°~128° C.,0.03____
D0.
--.__do
CH:
16____ —CH3 __________ -_ -—CH: .......... -. “43g
/CHr-CH:
17....
\
CH;
-—C»H~
_..--dn
152°-155° 0., o.o2____
Do.
14s°-151° 0., 0.03-"-
Do.
CHz-C?z
18.-.- -—-CH1CH=CEg__ -—CH;OH=CH¢-. ._-__dn
___--dn
I
.
19____ _c,m
-c~m
-_--_dn
oniomcmc?cooczmnuu 121°-124° 0., 0.03..--
Do.
20.... -cm
R
.__;.dn
-0H=00N(C2H.)= ............ -_ 185°-188°C.,0.6.____
Do.
2,411,062
9
‘
the solution is concentrated by evaporation to
amide may also be prepared more advantageously
dryness and heated for. some time to 50° C. with
according to the method described in Example 1.
the calculated quantity of phosphorus pentachlo
From the ethyl amino acetic diethyl amide ob
tainable as by-product it is possible to produce
ride. After having eliminated the phosphorus
oxychloride in vacuo one obtains the hydrochlo
compounds according to the present invention
when working in accordance with the methods of
the Examples 1 to 3 by interaction with chlor
acetic acid and by neutralisation with chlor
acetic ester, chloraceto-nitrile, etc.
ride of the N-ethyl-imino-di-n-butyric acid di
chloride which is introduced into an excess of a
diethyl amine solution, After having removed
the diethyl amine hydrochloride by filtration,
10 there is distilled in the high-vacuo. Thus the
EXAMPLE ‘5
N-ethyl-imino-di-n-butyric acid bis-diethyl amide .
is obtained in form of a colourless oil boiling
, 36 parts of a-N-ethyl-imino-butyric acid ethyl
at a pressure of 0.03 mm. at 133°-135° C.
The same product is also obtained by heating
amide acetic acid diethyl amide (see table Ex
ample 1) having the formula
10
.
'
'
the disodium salt of the N-ethyl-imino-di-n
butyric acid with diethyl carbamic acid chloride
to 150°-160° C. or by working inthe manner de
scribed in Example 3.
What we claim ,is:
are dissolved in .x'ylene, treated with 4 parts of
sodium amide and heated for some time on the
water-bath until no more ammonia is developed.
Then ‘the sodium compound is heated in the
autoclave at 180°-190° C. with 16.5 parts of po
20'
.
'
1. An imino-di-fatty acid amide of the for
mula
m-oRcoN
R:
After having separated 25
tassium ethyl sulfate.
/R:
the potassium sodium sulfate the solvent is dis
tilled oil and the N-ethyl-imino-butyric acid
RQ—GH.CO.N
\
acetic acid bis-diethyl amide is recti?ed in the
high-vacuo. B. P.o.o3 mm. 134°-1_'36° C.
The same compound can also be prepared ac 30 wherein R5 and R6 each represents a member
cording to anyone of the methods described in
selected from the group consisting of H and lower
the above process.
'
‘
alkyl, R0 represents a member selected from the
group consisting of lower ‘alkyl, allyl, benzyl,
Exim-Ls 6
35 phenethyl and cyclohexyl, R1 represents a mem
27.1"pai‘ts of a-imino-dipropionic acid bis-di-' ber selected from the group consisting of H, lower
alkyl and allyl, and R2, R3 and R4 each repre
ethyl amide oi the formula
sents a ‘member selected from the group consist
ing of lower alkyl and ally].
2. An imino-di-fatty acid amide of the for
40
mula
'
are heated for‘ several hours on the water-bath
with 13.5 parts of 85% formic acid and 20 parts
of 35% formaldehyde. Then 12 parts of concen 45
trated hydrochloric acid are added thereto. and
wherein R5 and Rs each represents a member
the formic acid as well as the excess of formalde
selected from the group consisting of H and lower
hyde are distilled oil. The residue is treated with
alkyl, and R0 represents a‘ member selected from
water and saturated with potassium hydroxide.
The formed N-methyl-imino-di-(propionic acid 50 the group consisting of lower alkyl, allyl, benz'yl,
phenethyl and cyclohexyl.
'diethylamide) is dissolved in benzene and dried
3. An imino-di-fatty acid amide of the for
over solid potassium hydroxide.- After distilla
tion of the solvent it is recti?ed in high-vacuo.
B. P.o.c1 mm. 133° C.
mula
'
Y
.
The same compound may also be produced ac; 65
cording to the method described in Example 2.
By methylation with dimethyl sulfate or methyl
iodide the same compound is obtained, while anal- '
wherein R5 and R6 each represents a member
ogous derivatives may be prepared by interac
tion with other alkylating agents or also with 60 ‘selected from the group consisting of H and lower
alkyl, and R0 represents a member selected from
aralkylating agents like diethyl sulfate,- ethyl‘
the group consisting of lower alkyl, allyl, benzyl,
chloride, benzyl chloride, phenyl ethyl bromide
and so on.
.
phenethyl and cyclohexyl.
‘
-
.
4. An imino-di-fatty acid amide of the for
EXAMPLE ‘7
mula
-
‘30 parts of a-N-ethyl-imino-di-n-butyric acid
R;—(|JH.'C0.N(C1H;)| _
’ diethyl ester of the formula
omomomoooom.
H‘CLN
' cmcmdmooocm.
(made from a-bromobutyric acid ethyl ester and
ethyl amine) are boiled under re?ux for several
Re-N
.
RPéH.CO.N(CHI)2
70,
wherein R5 ‘and Rs each represents a member
selected from the group consisting of H and lower
alkyl, and R0 represents a member selected from '
the group consisting of lower alkyl, allyl, benzyl,
hours with concentrated hydrochloric acid. Then 75 phenethyl and cyclohexyl.
‘
2,41 1,662
12
5. An imino-di-fatty acid amide of the .for
mula
group consisting of H, lower alkyl, and allyl and
R2, R3 and R4 each represents a member selected
from the group consisting of lower alkyl and allyl.
7. The imino-di-fatty acid amide of the fol
lowing formula
‘
cm-oncomcm'»
CH;(CH2)a—N
CHr
Y
CHr- 11.0 0.N(CH3)Z
10
wherein R0 represents a member selected from
mm. pressure of 132°-l35° C.
the group consisting of lower alkyl, allyl, benzyl,
_8. The imino-di-fatty acid amide of the fol
lowing formula
phenethyl and cyclohexyl, R1 represents a mem
ber selected from the group consisting of H, lower '
alkyl and allyl, and R2, R3 and R4 each repre
sents a member selected from the group consist
being a colorless liquid of the boiling point at 0.09
15
ing of lower alkyl and allyl.
6. An imino-di-i'atty acid amide of the for
being a colorless liquid of the boiling point at
mula
20 0.09 mm. pressure of 133°-136° C.
'
R
Rs
011.00.}:
9. The imino-di-fatty acid amide of the fol
lowing formula
/Rl
25
7 being a colorless liquid of the boiling point at 0.12
wherein R5 and Rs each represents a member
mm. pressure of 148°-151° C,
.
selected from the group consisting of H and lower
HENRY MARTIN.
alkyl, R1 represents a member selected from the 30
HANS GYSIN;
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