α-[4-(Dimethylamino)cyclohexyl]-α-(2-thienyl)-2-thiophenemethanol Chemische Eigenschaften,Einsatz,Produktion Methoden
Originator
Sorboquel,Schering,US,1960
Manufacturing Process
The requisite intermediate, ethyl 4-dimethylaminocyclohexylcarboxylate is
prepared as follows: 33 g of ethyl p-aminobenzoate dissolved in 300 cc of
absolute ethanol containing 16.8 cc of concentrated hydrochloric acid is
hydrogenated at 50 pounds hydrogen pressure in the presence of 2 g of
platinum oxide. The theoretical quantity of hydrogen is absorbed in several
hours, the catalyst removed by filtration and the filtrate concentrated to
dryness in vacuo. The residue is dissolved in water, made alkaline with
ammonium hydroxide and extracted with chloroform. After removal of the
solvent, the residual oil is distilled to yield ethyl 4-
aminocyclohexylcarboxylate, boiling point 114°C to 117°C/10 mm.
A mixture of 49 g of this ester compound, 76 g of 98% formic acid and 68 ml
of formalin solution is heated under reflux for 8 hours. The solvents are then
removed in vacuo on the steam bath, the residue dissolved in water, made
alkaline with ammonium hydroxide and extracted with chloroform. Removal of
the solvent and distillation in vacuo yields ethyl 4-
dimethylaminocyclohexylcarboxylate, boiling point 122°C to 125°C/10 mm.
To a solution of thienyl magnesium bromide prepared from 21.4 g of
magnesium and 144 g of 2-bromothiophene are added 39.8 g of ethyl 4-
dimethylaminocyclohexylcarboxylate. The mixture is allowed to warm to room
temperature and stirred for an additional six hours. The reaction mixture is
then decomposed with dilute ammonium chloride solution and extracted with
ether. The combined ether extracts are extracted thoroughly with 10%
hydrochloric acid and the acid solution made alkaline with ammonium hydroxide. The aqueous solution is extracted with chloroform which is then
washed with water, dried and evaporated to a residue in vacuo.
Recrystallization of the residue from hexane yields α,α1-dithienyl-4-
dimethylaminocyclohexyl carbinol, melting point 156°C to 157°C after
recrystallization from benzene.
Therapeutic Function
α-[4-(Diethylamino)cyclohexyl]-α-2-thienyl-2-thiophenemethanol
α-[4-(Dimethylamino)cyclohexyl]-α-(2-thienyl)-2-thiophenemethanol Upstream-Materialien And Downstream Produkte
Upstream-Materialien
Downstream Produkte
