The Manufacture of Methenyldi-para and Ortho-phenetidine and Anisidine.
Year: 1898

page_text: Date of Application, 28th Apr., 1898
Complete Specification Left, 26th Jan., 1899--Accepted, 28th Apr., 1899
PROVISIONAL SPECIFICATION.
The Manufacture of Methenyldi-para and Ortho-phenetidine and
Anisidine.
I, CARL GOLDSCHMIDT, Ph.D., of 5, Marienstrasse, Frankfort on Main, in the
Empire of Germany, Chemist, do hereby declare the nature of my invention to
be as follows:-
When 34-6 kilogrammes of paraphenetidine in alcoholic solution are heated for
10 minutes with 14.8 kilogr. of ortho-formnic ether upon the waterbath and the
product of the reaction is poured into dilute soda lye, an oil separates which in a
short time coagulates. Crystallization is effected from the dilute alcohol and the
product is fusible at 114° Centigrade. The hydrochlorate is fusible at a temperature
of upwards of 200° Centigrade. The acetate dissolves in water with difficulty..
In preparing the compound phenetidine and ortho-formic ether in a neutral
solution may, if preferred, be heated direct, but the result is far less satisfactory.
From para-anisidine and ortho-formic ether a compound fusible at 119° Centigrade
A similar compound cannot be successfully obtained from ortho-forme
O para-amido-phenol-hydrochlorate.
The compound possesses the property of rendering the skin insensitive while
taken at a small dose it acts as a preventative of sea-sickness.
Instead of the para compounds, ortho compounds may be used, in which case the
time of heating should be somewhat increased.

page_text: 25 kilogrammes of ortho-anisidine is heated for half an hour along with 16 kilo-
grammes of ortho-formic ether, either without any solvent, or in alcohol benzol,
toluol or xylol.
The product is poured into ice-cold water and the coagulated matter resulting is
filtered off. It is crystallized out of the alcohol twice and has a fusion point of
106° Centigrade.
It is soluble with difficulty in water, but is readily soluble in organic solvents. It
yields white crystals. The sulphate of this base is very readily soluble in water
and it is purified by dissolving in alcohol and precipitating in ether.
The Manufacture of Methenyldi-para and Ortho-phenetidine and
Anisidine.
I, CARL GOLDSCHMIDT, Ph.D., of 5, Marienstrasse, Frankfort-on-Main, in the
Empire of Germany, 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 :—…..
When 34.6 kilogrammes of paraphenetidine in alcoholic solution are heated for
10 minutes with 14.8 kilos. of ortho-formic ether upon the water bath and the
product of the reaction is poured into dilute soda lye; an oil separates which in a
short time coagulates.
Crystallization is effected from dilute alcohol and the product is fusible at 114°.
Centigrade. The hydrochlorate is fusible at a temperature of upwards of 200° Centi-
grade. The acetate dissolves in water with difficulty.

page_text: In preparing the compound phenetidine and ortho-formic ether may, if preferred,
be heated direct and the product of the reaction poured into a neutral solution, but
the result is far less satisfactory.
From para-anisidine and ortho-formic ether a compound fusible at 119° Centigrade
para-ammpyutoemorate.
The compound possesses the property of rendering the skin insensitive while a
small dose acts as a preventative of sea-sickness.
Instead of the "para" compounds, "ortho" compounds may be used, in which
case the time of heating should be somewhat increased.
25 kilogrammes of ortho-anisidine is heated for half an hour along with 16 kilo-
grammes of ortho-formic ether, either without any solvent, or in alcohol, benzol,
toluol, or xylol.
•>
The product is poured into ice-cold water and the coagulated matter resulting is
filtered off. It is crystallized out of alcohol twice and has a fusion point of
106° Centigrade.
It is soluble with difficulty in water, but readily soluble in organic solvents. It
yields white crystals. The sulphate of this base is very readily soluble in water and
it is purified by dissolving in alcohol and precipitating in ether.

page_text: 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 is :-
1. The manufacture and production from para-phenetidine or para-anisidine
and ortho-formic ether of a compound more especially intended for use as an
anaesthetic.
2. The manufacture and production from ortho-phenetidine or ortho-anisidine
and ortho-formic ether of a compound more especially intended for use as an
anaesthetic.