Manufacture of New Products from Piperidine
Year: 1897

page_text: Date of Application, 20th Feb., 1897
Complete Specification Left, 19th Nov.; 1897-Accepted; 24th Dec., 1897
Date of Application, 20th Feb., 1897
Complete Specification Left, 19th Nov.; 1897-Accepted; 24th Dec., 1897
PROVISIONAL SPECIFICATION.
"Manufacture of New Products from Piperidine."
We, JOSEPH TURNER AND COMPANY LIMITED of Queensferry, Flintshire, Manu-
facturers, and PHILIP SCHIDROWITZ of 57 Chancery Lane, London, Research
Chemist and OTTO ROSENHEIM of 57 Chancery Lane, London, Research Chemist,
do hereby declare the nature of this invention to be as follows:-
This invention relates to the manufacture of new products from piperidine.
These new products are obtained by the action of carbonic acid, tartaric acid and
succinic acid on piperidine, the result being new salts or bodies, which are
believed to possess valuable pharmacological and therapeutic properties.
When acting upon piperidine by carbonic acid the piperidine may be employed
either alone or dissolved in a suitable solvent such for example as acetone, ether
or petroleum spirit and the carbonic acid may be either moist or dry. A pro-
duct is formed, with evolution of heat, which is a white crystalline body in
needles or plates having a melting point of 79° 80° C. This body distills with-
out decomposition and is easily soluble in water. It decomposes by the action of
weak acids with evolution of carbonic acid. It is easily soluble in cold or hot
alcohol, methyl and amyl alcohols and chloroform, and less soluble in cold ether,
petroleum spirit and acetone. This body we believe piperidyl carbamate of
piperidine and it corresponds to the formula:

page_text: ( = 1 molecule) of succinic acid and 170 parts (= 2 molecules) of piperidine at
a water bath temperature. On cooling the melt is recrystallized from alcohol.
The product which is a succinate of piperidine is in the form of white pris-
matic plates. It has a melting point of 1420-143°C., it is soluble in water and
hot alcohol but not easily soluble in cold alcohol.
J. C. MEWBURN & ELLIS,
55 and 56 Chancery Lane, London. Chartered Patent Agents.
"Manufacture of New Products from Piperidine."...
We, JOSEPH TURNER AND COMPANY LIMITED of Queensferry, Flintshire, Manu-
facturers, and PHILIP SCHIDROWITZ of 57 Chancery Lane, London,. Research
Chemist, and OTTO ROSENHEIM of 57 Chancery Lane, London, Research 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 follow-
ing statement:—
This invention relates to the manufacture of new products from piperidine.
These new products are obtained by the action of carbonic acid, tartaric acid and
succinic acid on piperidine, the result being new salts or bodies which are
believed to possess valuable pharmacological and therapeutic properties.
When acting upon piperidine by carbonic acid the piperidine may be employed
either alone or dissolved in a suitable solvent such for example as acetone, ether
or petroleum spirit and the carbonic acid may be either moist, or dry. A pro-
duct is formed with evolution of heat, which is a white crystalline body in
needles or plates having a melting point of 79° 80° C. This body distils with-
out decomposition and is easily soluble in water. It decomposes by the action of
weak acids with evolution of carbonic acid. It is readily soluble in cold or hot
alcohol, methyl and amyl alcohols and chloroform, and less soluble in cold ether,
petroleum spirit and acetone. This body is piperidyl carbamate of piperidine and
it corresponds to the formula:-
-
"Manufacture of New Products from Piperidine."...
We, JOSEPH TURNER AND COMPANY LIMITED of Queensferry, Flintshire, Manu-
facturers, and PIIILIP SCHIDROWITZ of 57 Chancery Lane, London,. Research
Chemist, and OTTO ROSENHEIM of 57 Chancery Lane, London, Research 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 follow-
ing statement:―
This invention relates to the manufacture of new products from piperidine.
These new products are obtained by the action of carbonic acid, tartaric acid and
succinic acid on piperidine, the result being new salts or bodies which are
believed to possess valuable pharmacological and therapeutic properties..
When acting upon piperidine by carbonic acid the piperidine may be employed
either alone or dissolved in a suitable solvent such for example as acetone, ether
or petroleum spirit and the carbonic acid may be either moist, or dry. A pro-
duct is formed with evolution of heat, which is a white crystalline body in
needles or plates having a melting point of 79° 80° C. This body distils with-
out decomposition and is easily soluble in water. It decomposes by the action of
weak acids with evolution of carbonic acid. It is readily soluble in cold or hot
alcohol, methyl and amyl alcohols and chloroform, and less soluble in cold ether,
petroleum spirit and acetone. This body is piperidyl carbamate of piperidine and
it corresponds to the formula:-
N.CH10
OH.NH.CH10
It can be made in several ways. According to one way which we will give
as an example 10 kilogrammes of piperidine are dissolved in 5 kilogrammes of
acetone in a suitable vessel, preferably provided with cooling apparatus, and the
solution is saturated with carbonic acid, the saturation being preferably effected
by passing the carbonic acid into the solution. The salt crystallizes out and is
L
1:
1
OH.NH.CH10
It can be made in several ways. According to one way which we will give
as an example 10 kilogrammes of piperidine are dissolved in 5 kilogrammes of
acetone in a suitable vessel, preferably provided with cooling apparatus, and the
solution is saturated with carbonic acid, the saturation being preferably effected
by passing the carbonic acid into the solution. The salt crystallizes out and is
Altere
off by any ordinary method and is recrystallized if necessary. According
to another way the piperidine is spread or distributed in shallow vessels or on trays
in an air tight chamber and exposed to the action of carbonic acid gas which is
introduced to the chamber preferably at the upper part. The chamber may be
provided with a safety valve and pressure gauge and with a door or doors for the
introduction and removal of the trays.
When acting upon piperidine by tartaric acid we make an approximately satu-
rated cold solution of 75 parts (= 1 molecule) of tartaric acid and then add 42
parts (1 molecule) of piperidine. Heat is evolved. On cooling, the salt is

page_text: recrystallized from hot alcohol or other suitable solvent and tartrate of piperidine
is obtained in the form of prismatic plates: The product has a melting point
of 1360-137° C. andi is readily soluble in cold water and corresponds to the formula
CH N.C,H,O.
11
When acting upon piperidine with succinic acid we melt together 118 parts
(1 molecule) of succinic acid and 170 parts ( = 2 molecules) of piperidine at
a water bath temperature. On cooling the melt is recrystallized from alcohol or
other suitable solvent. The product which is a succinate of piperidine is in the
form of white prismatic plates. It has a melting point of 1420-143° C., it is
soluble in water and hot alcohol but not readily soluble in cold alcohol and cor-
responds to the formula (CHN) ¸.CHÃO̟
Having now particularly described and ascertained the nature of our said in-
vention and in what manner the same is to be performed, we declare that what we
claim is:
1. The manufacture of a new product from piperidine by treating piperidine
either alone or dissolved in a suitable solvent with carbonic acid, substantially as
hereinbefore described.
2. The manufacture of a new product from piperidine by dissolving piperidine
in acetone or other solvent and then saturating the solution with carbonic acid,
substantially as hereinbefore described.
3. The manufacture of a new product from piperidine by spreading the piperi-
dine in shallow vessels or on trays in an air tight chamber and subjecting it to
the action of carbonic acid introduced into the said chamber, substantially as
hereinbefore described.
4. As a new product piperidyl carbamate of piperidine.
5. The manufacture of a new product from piperidine by treating piperidine
with tartaric acid, substantially as hereinbefore described.
6. As a new product tartrate of piperidine.
7. The manufacture of a new product from piperidine by treating piperidine
with succinic acid, substantially as hereinbefore described.
8. As a new product succinate of piperidine.
1
100
1007
J. C. MEWBURN & ELLIS,
55 and 56 Chancery Lane, London. Chartered Patent Agents.