Sodium Hydroxide → [3-(5-Methoxy-benzofuran-2-yl)-3-phenyl-propyl]-methyl-amine

Participants

Reaction Conditions

Reaction Steps

5-methoxybenzofuran (0.48 g) and trifluoro-acetic acid 3-[methyl-(2,2,2-trifluoro-acetyl)-amino]-1-phenyl-propyl ester (0.48 g) were mixed and heated in a sealed tube at 110° C. for 90 minutes. Upon cooling, the reaction mixture was taken up in methanol and treated with excess 1N sodium hydroxide solution, sufficient to form a strongly basic solution. After stirring for 20 minutes, the reaction mixture was concentrated at reduced pressure to remove the bulk of the methanol. The resulting mixture was partitioned between ethyl acetate and water. The layers were separated and the organic layer was evaporated to dryness. Purification by column chromatography (silica gel, dichloromethane (130):methanol (10):ammonium hydroxide (1)) followed by preparative tlc afforded [3-(5-Methoxy-benzofuran-2-yl)-3-phenyl-propyl]-methyl-amine (M+H=296) as the major component.

Provenance & Evidence