[2-hydroxy-3-(m-tolyloxy)propyl]isopropylammonium chloride

Originator

Doberol,Boehringer, Ing.

Manufacturing Process

59 g (1 mol) of isopropylamine in 60 ml of water are added to a solution of 82 g (0.5 mol) of 3-(3'-methylphenoxy)propylene oxide (prepared from 3-methyl phenol and epichlorohydrin) in 400 ml of ethanol. After the exothermic reaction has subsided, the mixture is heated for 2 hours at 60°C. After distillation of the volatile components, the free base remains as a solid residue. It is dissolved in hydrochloric acid the acid solution is extracted with ether and then made alkaline with caustic soda solution. The base crystallizes out and is dried over P2O5; 101.9 g (91.3% of theory) of 1-(isopropylamino)- 3-(m-tolyloxy)-2-propanol being obtained; it is recrystallized from ethyl acetate/petroleum ether, and then has MP: 75-76°C. Upon addition of ethereal hydrogen chloride to an alcoholic solution of the base, the hydrochloride precipitates, and after recrystallization from alcohol/ether, has MP: 120- 121°C.

Therapeutic Function

Beta-adrenergic blocker