Hydrogen Bromide → HCID 18933633, compound

Participants

Reaction Steps

A mixture of 2-[2-(N-benzyl-N-methylamino)ethoxy]-5-methoxy-N,N-dimethylbenzylamine (1.0 g), aqueous hydrobromic acid (10 ml, 48%) and hypophosphorous acid (0.05 ml, 50% by weight aqueous solution) was boiled under reflux under nitrogen for 1 hour. The mixture was evaporated to dryness under reduced pressure and the residue was neutralised with saturated sodium bicarbonate solution and then basified to pH 9 with 2M sodium hydroxide solution. The mixture was extracted with dichloromethane to give a gum. The gum was purified by flash column chromatography on silica using ethyl acetate/methanol/triethylamine (18:2:1) as the mobile phase to give an oil which was dissolved in ether and acidified with ethereal hydrogen chloride to give a solid which was collected by filtration and then recrystallised from propan-2-ol to give 4-[2-(N-benzyl-N-methylamino)ethoxy]-3-(dimethylaminomethyl)phenol dihydrochloride, m.p. 199°-200° C.

Provenance & Evidence