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

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Reaction Conditions

Reaction Steps

A mixture of 6-methoxy-2-(4-(4-phenylbenzoylamino)butyl)-1,2,3,4-tetrahydroisoquinoline (1.18 g, 2.8 mmol) and dichloromethane (50 ml) was treated dropwise with a solution of boron tribromide in dichloromethane (1M; 8.4 ml). The mixture was stirred at 20° C. for 18 h, then poured into a mixture of ice (100 g) and 0.880 ammonia (100 ml). Resulting mixture was extracted with dichloromethane (3×50 ml) and the combined extracts were dried (Na2SO4) and evaporated in vacuo. The residue was triturated with ether to give the title compound (0.86 g, 77%) as a yellow solid.

Provenance & Evidence