6-Methoxy-1,2,3,4-tetrahydroisoquinoline → 6-Methoxy-2-(4-(4-phenylbenzoylamino)butyl)-1,2,3,4-tetrahydroisoquinoline

Participants

Reaction Conditions

Reaction Steps

A mixture of 6-methoxy-1,2,3,4-tetrahydroisoquinoline (1.00 g, 6.2 mmol), 4-(4-phenylbenzoylamino)butyraldehyde (1.64 g, 6.2 mmol), sodium triacetoxyborohydride (1.94 g, 9.2 mmol) and dichloromethane (50 ml) was stirred at 20° C. for 18 h. Resulting solution was partitioned between saturated aqueous NAHCO3 (50 ml) and dichloromethane (3×50 ml). Combined organic extracts were dried (Na2SO4) and evaporated in vacuo to give a solid. Trituration with 1:1 dichloromethane-ether gave the title compound (0.80 g, 32%).

Provenance & Evidence