Manufacture of Derivatives of a Body obtained from Hydrobromide of Dibromotriacetonamine.
Year: 1899

page_text: Date of Application, 4th Mar., 1899
Complete Specification Left, 20th Nov., 1899-Accepted, 6th Jan.,
1900
Manufacture of Derivatives of a Body obtained from Hydrobromide
of Dibromotriacetonamine.
I, DR. HERMANN PAULY, of Basle, Switzerland, Chemist, do hereby declare the
nature of this invention to be as follows:-
By treating triacetonamine with bromine in solution of strong hydrobromic acid I
have prepared the hydrobromide of a dibromotriacetonamine (compare Berichte der
deutschen chemischen Gesellschaft XXXI., 668). I have further stated that by
digesting this hydrobromide with ammonia the two bromine atoms which have.
entered the nucleus of the compound are replaced by the group NH, a new base
being formed whose composition corresponds with the empirical formula CH₁N₂O.
and to which I have given the name iminotriacetonamine; I have not yet arrived at
a definite decision as to the rational constitution of this new base.
I have now found that N-alkyl¹ derivatives of this iminotriacetoamine may be
obtained by the following methods.
(1) By treating iminotriacetonamine with alkyl halides such as methyliodide, etc.,
and then decomposing the products formed by means of an alkali.
(2.) By treating dibromotriacetonamine or its salts with primary amines, such as
methylamine, etc.
The bases obtained in the manner indicated in (2) are isomeric with those obtained
by the first method.
The N-alkyl derivatives of iminotriacetonamine are of great medicinal value owing
to their property of forming easily soluble salts with uric acid.
I have moreover found that certain valuable reduction products are obtained from
the derivatives above mentioned,
(1) By treating iminotriacetonamine or its alkyl derivatives with reducing agents,
such as sodium amalgam.
(2) By treating with alkyl halides the product of the reduction of iminotriaceton-
amine.
These new reduction products of iminotriacetonamine and of its N-alkyl derivatives
also possess the valuable property of forming easily soluble uric acid salts, some of
them even in a higher degree than the primary derivatives above described.
Dated this 4th day of March 1899.
ADEL e TMDX
BEL &
TMDAX
Agents for the Applicant.
Manufacture of Derivatives of a Body obtained from Hydrobromide
of Dibromotriacetonamine.
I, DR. HERMANN PAULY, of Basle, Switzerland, Chemist, do hereby declare the
nature of this invention and in what manner the same is to be performed to be
particularly described and ascertained in and by the following statement:-
By treating triacetonamine with bromine in solution of strong hydrobromic acid I
have prepared the hydrobromide of a dibromotriacetonamnine (compare Berichte der
deutschen chemischen Gesellschaft XXXI., 668). I have further stated that by digesting
this hydrobromic salt with ammonia the two bromine atoms which have entered the
[Price 8d1

page_text: As to the
nucleus of the compound are replaced by the group NH, a new base being formed,
the composition of which corresponds with the empirical formula C,H₁N, and to
which I have in the first instance given the name iminotriacetonamine.
rational constitution of this new base I have, since filing the Provisional Specification
arrived at a definite decision. My recent researches have shewn that the so-called
iminotriacetonamine does no more contain the triacetonamine-nucleus, but is the
amide of a pyrrolin-carboxylic acid and is formed according to the following
I have now found that alkyl-derivatives of this amide of a-tetramethylpyrrolin-ẞ-
carboxylic acid, (called before iminotriacetonamine) may be obtained by the following
methods:
I. By treating the above mentioned amide with alkylhalides, such as methyliodide
&c. and then decomposing the products formed by means of an alkali.
II. By treating dibromotriacetonamine or its salts with amines, such as methyl-
amine &c.
The bases obtained in the manner indicated in II are isomeric with those obtained
by the method I.
The alkyl-derivatives of the amide of a-tetramethylpyrrolin-3-carboxylic acid are
of great medicinal value owing to their property of forming easily soluble salts with
uric acid.
I have inoreover found that certain valuable reduction products are obtained
from the derivatives above mentioned :
(1). By treating the amide of a-tetramethyl-pyrrolin-3-carboxylic acid or its alkyl-
derivatives with reducing agents, such as sodium amalgam.
(2) By treating with alkyl-halides the product of the reduction of the amide of
a-tetramethylpyrrolin-ẞ-carboxylic acid.
These new reduction products of the new amide and of its alkyl- derivatives equally
possess the valuable property of forming easily soluble uric acid salts, some of them
even in a higher degree than the primary derivatives above described.
The formation of the new derivatives and their constitution is indicated by the
following equations.
A FORMATION
BALLA
EUE ARDLY FOXBO

page_text: In the above equations R represents an alkyl-group, and R1 and R2 two different
or the same alkyl-groups.
In order to illustrate further the invention the following examples are given.

page_text: Production of N-methyl-a-tetramethylpyrrolidin-3-carboxylamide from a-tetra-
methylpyrrolidin-ẞ-carboxylamide (Compare equation B II).
1 part by weight of a-tetramethylpyrrolidin-B-carboxylamide and 1 part of methyl-
iodide are dissolved in 3 parts of methyl alcohol. After standing for several days a
well crystallized methoiodide separates which on addition of alkali yields N-methyl-
a-tetramethylpyrrolidin-3-carboxylamide, which has been found identical with the
compound obtained as described in the preceding example by the reduction of
N-methyl-a-tetramethylpyrrolin-ß-carboxylamide.
If in the preceding example for a-tetramethylpyrrolidin-3-carboxylamide is
substituted the corresponding methylamide there is obtained N-methyl-a-tetra-
methylpyrrolidin-3-carboxylmethylamide which is shewn in the preceding example
can also be produced by reduction of N-methyl-a-tetramethylpyrrolin-B-carboxyl-
methylamide.
Having now particularly described and ascertained the nature of this inven-
tion and in what manner the same is to be performed, I declare that what I
claim in respect of an amide of a pyrrolin carboxylic acid formerly known as
iminotriacetonamine is:-
1. The herein described manufacture of alkyl-derivatives of the said a-tetramethyl-
pyrrolin-ẞ-carboxylamide.
a) by treating the said carboxylamide or corresponding carboxylalkylamides
respectively with alkyl halides and decomposing the products thus obtained by
means of alkalies.
b) by treating dibromotriacetonamine and its salts with amines such 88
methylamine.
2. The alkyl-derivatives manufactured as above set forth.
3. The herein described manufacture of reduction products of a-tetramethyl-
pyrrolin-6-carboxylamide and of its alkyl-derivatives by treating these compounds
with reducing agents.
4. The herein described manufacture of alkyl-derivatives of the reduction-products
obtained from a-tetramethylpyrrolin-3-carboxylamide and from a-tetramethyl-
pyrrolin-ẞ-carboxylalkylamides by treating these reduction products with alkyl
halides.
5. The reduction-products and their alkyl-derivatives manufactured as above set
forth.
73
J
6041
1000