Clobutinol

Clobutinol Basic information
Product Name:Clobutinol
Synonyms:Clobutinol (base and/or unspecified salts);1-(p-Chlorophenyl)-4-(dimethylamino)-2,3-dimethyl-2-butanol;4-Chloro-α-[2-(dimethylamino)-1-methylethyl]-α-methylphenethyl alcohol;4-Chloro-α-methyl-α-[2-(dimethylamino)-1-methylethyl]phenethyl alcohol;1-(4-chlorophenyl)-4-(dimethylamino)-2,3-dimethyl-butan-2-ol;1-(4-chlorophenyl)-4-(dimethylamino)-2,3-dimethylbutan-2-ol;1-p-Chlorophenyl-2,3-dimethyl-4-dimethylamino-2-butanol;2-(p-Chlorobenzyl)-3-dimethylaminomethyl-2-butano
CAS:14860-49-2
MF:C14H22ClNO
MW:255.78
EINECS:238-926-4
Product Categories:
Mol File:14860-49-2.mol
Clobutinol Structure
Clobutinol Chemical Properties
Boiling point bp12 179-180°
density 1.0373 (rough estimate)
refractive index 1.6330 (estimate)
pka14.63±0.29(Predicted)
Safety Information
MSDS Information
Clobutinol Usage And Synthesis
OriginatorSilomat,Boehringer Ingelheim,Switz.,1960
DefinitionChEBI: 1-(4-chlorophenyl)-4-(dimethylamino)-2,3-dimethyl-2-butanol is an organic amino compound and a member of benzenes.
Manufacturing ProcessA solution of 0.2 mol (33 g) of 3-methyl-4-dimethylamino-butanone-(2) [produced according to Mannich, Arch. Pharm., vol. 265, page 589 (1927)] in 50 cc absolute ether was added dropwise, while stirring and cooling with ice, to a Grignard solution of 0.4 mol p-chlorobenzylmagnesium-chloride which was produced from 64.5 g p-chlorobenzyl-chloride and 9.8 g magnesium in 200 cc absolute ether. The reaction product was heated for an additional onehalf hour under reflux to bring the reaction to completion, and thereafter the reaction mixture was decomposed into an ether phase and an aqueous phase with about 50 cc concentrated hydrochloric acid and about 200 g ice. The ether phase was discarded and the aqueous phase was adjusted to an alkaline pH with ammonia and then thoroughly extracted with ether. After concentrating the united, dried ether extract solutions, the oily residue was fractionally distilled. The reaction product was obtained in the form of a colorless oil having a boiling point of 179° to 181°C. The yield was 48.5 g corresponding to 95% of theory.
The hydrochloride addition salt of the above reaction product was prepared in customary fashion, that is, by reaction with hydrochloric acid, followed by fractional crystallization from a mixture of alcohol and ether. The two possible racemic forms were obtained thereby. The difficultly soluble racemate had a melting point of 169° to 170°C and the more readily soluble racemate had a boiling point of 145° to 148°C.
Therapeutic FunctionAntitussive
Clobutinol Preparation Products And Raw materials
Raw materialsMagnesium-->Hydrochloric acid-->4-Chlorobenzyl chloride
Tenofovir disoproxil fumarate Clobutinol p-chloro-alpha-[2-(dimethylamino)-1-methylethyl]-alpha-methylphenethyl alcohol hydrochloride Phenethyl alcohol 1-(4-Chlorophenyl)-2-methyl-2-propanol 2,3-DIMETHYL-2-BUTANOL

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