Hydrochloric Acid → 1-(N-benzyloxycarbonyl-p-toluidinomethyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride

Participants

Reaction Steps

A mixture of hydrochloride and phosphate of 1-(N-benzyloxycarbonyl-p-toluidinomethyl)-6,7-dimethoxy-3,4-dihydroisoquinoline (4.6 g) was dissolved in 99% ethanol (45 ml). To the solution was added sodium borohydride (0.8 g) with stirring under ice cooling, and the mixture was stirred for 1.5 hours. The reaction mixture was concentrated to dryness under reduced pressure and to the residue was added water. The mixture was saturated with sodium chloride and extracted with ethyl acetate. The extract was dried and the solvent was distilled off. The oil obtained was treated with ethanol containing hydrochloric acid to give 1-(N-benzyloxycarbonyl-p-toluidinomethyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride (2.3 g), mp 189° to 190° C.

Provenance & Evidence