Improvements in the Manufacture of Phenacetine Derivatives.
Year: 1890

page_text: Date of Application, 15th Apr., 1890
Complete Specification Left. 31st Dec., 1890-Accepted, 31st Jan., 1891
PROVISIONAL SPECIFICATION.
Improvements in the Manufacture of Phenacetine Derivatives.
1, BENJAMIN WILLCOX, of 47 Lincoln's Inn Fields, in the County of Middlesex,
Patent Agent, do hereby declare the nature of this invention (which has been
communicated to me from abroad by The Farbenfabriken vormals Friedrich
Bayer & Co., of Elberfeld, in the Empire of Germany,) to be as follows:-
My foreign correspondents have discovered that the para aceto phenetidine
alkylised by nitrogen can be obtained by treating the sodium combination of
phenacetine with alkyl haloids. In order to obtain the methyl phenacetine the
process is conducted as follows for example :-
Para aceto phenetidine is dissolved in xylol and to the boiling solution the
calculated quantity (1 molecular proportion) of sodium is added; the phenacetine
sodium formed with generation of hydrogen separates immediately from the liquid
in the form of white needles and is directly mixed with one molecular proportion of
methyl iodide. The transposition proceeds immediately with formation of sodium
iodide. Methyl phenacetine results according to the following equation
PROVISIONAL SPECIFICATION.
Improvements in the Manufacture of Phenacetine Derivatives.
1, BENJAMIN WILLCOX, of 47 Lincoln's Inn Fields, in the County of Middlesex,
Patent Agent, do hereby declare the nature of this invention (which has been
communicated to me from abroad by The Farbenfabriken vormals Friedrich
Bayer & Co., of Elberfeld, in the Empire of Germany,) to be as follows:-
My foreign correspondents have discovered that the para aceto phenetidine
alkylised by nitrogen can be obtained by treating the sodium combination of
phenacetine with alkyl haloids. In order to obtain the methyl phenacetine the
process is conducted as follows for example
Para aceto phenctidine is dissolved in xylol and to the boiling solution the
calculated quantity (1 molecular proportion) of sodium is added; the phenacetine
sodium formed with generation of hydrogen separates immediately from the liquid
in the form of white needles and is directly mixed with one molecular proportion of
methyl iodide. The transposition proceeds immediately with formation of sodium
iodide. Methyl phenacetine results according to the following equation
OC₂ H,
/OC, H.
C. H₁
+ ICH, CH,
===
+ INa
Na
CH,
N
COCH,
COCH,
as the chief product of the reaction together with a small quantity of another oily
substance not yet defined.
At a
In order to isolate the methyl phenacetine it is separated by filtration from the
sodium iodide distilled in a current of steam to remove the xylol the residual oil
being dried and distilled under atmospheric pressure or in a vacuum.
temperature of from 295 to 305 degrees Centigrade methyl phenacetine passes over
in the form of a colourless oil which solidifies after standing for a time. By
spreading it out on earthenware plates or pressing, the crystalline mass is separated
from the adhering oil (above mentioned bye product) and again purified by solution
in ether or petroleum ether. Colourless crystals are thus obtained whose melting
point is from about 39-41 degrees Centigrade and which are moderately soluble
in water or readily soluble in ether dissolving agents. When the methyl iodide in
this example is replaced by the equivalent quantity of ethyl iodide the ethyl
phenacetine is obtained in the form of a slightly yellow oil boiling at from 330 to
335 degrees Centigrade and which solidifies after distillation. It is moderately
soluble in ether dissolving agents but is soluble with difficulty in water and forms
with hydrochloric acid a hydrochloric acid salt not readily soluble.
This product is valuable for pharmaceutical purposes.
Dated thin 15th dor of Anril 1800

page_text: COMPLETE SPECIFICATION.
Improvements in the Manufacture of Phenacetine Derivatives.
I BENJAMIN WILLCOX of 47 Lincoln's Inn Fields in the County of Middlesex,
Patent Agent, do hereby declare the nature of this invention which has been
communicated to me from abroad by The Farbenfabriken vorinals Friedrich Bayer
& Co. of Elberfeld in the Empire of Germany and in what manner the same is to
be performed to be particularly described and ascertained in and by the following
statement:-
My foreign correspondents have discovered that the alkylized para aceto-
-
-
-
phenetidines (C, H. – O – C, H. – N
Cx Hy
\COCH
can be obtained by treating
the sodium derivative of phenacetine with alkyl haloids. In order to obtain methyl-
phenacetine the process is conducted as follows for example:
Para-aceto-phenetidine (phenacetine) is dissolved in xylene and the calculated
quantity (one molecular proportion) of sodium is added to the boiling solution the
sodium phenacetine which forms with evolution of hydrogen separates immediately
from the liquid in white needles and is directly mixed with one molecular propor-
tion of methyl iodide. Action takes place immediately sodium iodide and
methylated phenacetine being produced according to the following equation.

page_text: Second. As new articles of manufacture the
described.
Dated this 31st day of December 1890
new products hereinbefore
J. H. JOHNSON & Co.,
47, Lincoln's Inn Fields, London, Agents.