tolpropamine hydrochloride

Originator

Tolpropamine,Hoechst (Aventis)

Manufacturing Process

The Grignard solution (prepared from 53 g bromtoluene and 7.2 g magnesium in 300 ml of ether) was added dropwise to a solution of 35 g β- dimethylaminopropiophenone in 50 ml ether. The mixture was refluxed for 3 hours. Then the liquid phase was added to 500 parts of ice and 100 parts concentrated hydrochloric acid. 1-Phenyl-1-p-tolyl-3-dimethylaminopropanol-1 was crystallized. M.P. of hydrochloride of 1-phenyl-1-p-tolyl-3- dimethylaminopropanol-1 185°C.
10 g of 1-phenyl-1-p-tolyl-3-dimethylaminopropanol-1 was dissolved in 30 ml of 85% phosphoric acid and the solution was heated at 130-135°C for 1 hour. After cooling to the mixture was added a water and an aqueous solution of sodium hydroxide. γ-Phenyl-γ-p-tolylallyldimethylamine was extracted with ether and extract was dried with sodium sulfate. γ-Phenyl-γ-p-tolylallyldimethylamine hydrochloride was hydrogenated with palladium catalyst. γ-Phenyl-γ-p-tolyl-3-dimethylaminopropan obtained has melting point 156°C.

Therapeutic Function

Antihistaminic, Antipruritic