Hydrochloric Acid → 1-(p-Chloroanilinomethyl)-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline hydrochloride

Participants

Reaction Conditions

Reaction Steps

A mixture of 1-(N-benzyloxycarbonyl-p-chloroanilinomethyl)-6,7-dibenzyloxy-1,2,3,4-tetrahydroisoquinoline hydrochloride (1.1 g), acetic acid (11 ml) and conc. hydrochloric acid (11 ml) was heated for 2 hours at 100° C. The reaction mixture was concentrated to dryness under reduced pressure and the residue was washed with ethyl acetate and ether and pulverized to give crude 1-(p-chloroanilinomethyl)-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline hydrochloride. The product was converted into its p-toluenesulfonate and then again converted into its hydrochloride to give a pure product, mp 91° to 93° C. The product was identified by means of comparison with an authentic sample prepared by another process by its infrared absorption spectrum and nuclear magnetic resonance spectrum.

Provenance & Evidence