N-[2-(4-benzyloxy-3-methoxyphenyl)ethyl]-1-(2-methoxyphenyl)cyclopropane carboxamide → 7-Benzyloxy-6-methoxy-1-[1-(2-methoxyphenyl)cyclopropyl]-3,4-dihydroisoquinoline

Participants

Reaction Steps

A mixture of N-[2-(4-benzyloxy-3-methoxyphenyl)ethyl]-1-(2-methoxyphenyl)cyclopropane carboxamide (30.3 g) in acetonitrile (450 ml) and phosphoryl chloride (50 ml) was heated under reflux for 80 minutes. The solvent was evaporated in vacuo below 50° C. and the residue washed with ethyl acetate and then stirred with ethyl acetate (300 ml) and ice-cold 5% aqueous ammonia solution (200 ml) for 10 minutes. The organic layer was dried over potassium carbonate and the solvent removed by evaporation to give 7-benzyloxy-6-methoxy-1-[1-(2-methoxyphenyl)cyclopropyl]-3,4-dihydroisoquinoline.

Provenance & Evidence