Acetic Acid → HCID 9843596, compound

Participants

Reaction Steps

A slurry of 5-benzyloxyindole (6.85 g, 30.7 mmol) in methanol (50 mL) was added to a 25 wgt % solution of sodium methoxide in methanol (115 mL) at 5° C. under argon. 1-Benzyl-4-piperidone (5.8 g, 30.7 mmol) was added in one portion and the suspension heated at reflux for 16 h, cooled and diluted with a mixture of dichloromethane (100 mL) and methanol (150 mL). The solution was acidified to pH 5 with glacial acetic acid, concentrated to 100 mL, diluted with water (750 mL) and extracted with ethyl acetate (3×200 mL). The combined organic layers were washed with water (100 mL) and brine (100 mL) and dried (Na2SO4). Filtration and concentration in vacuo gave the title compound as a yellowrange solid (10.6 g, 87%). MS(ES) m/e 395.2 [M+H]+.

Provenance & Evidence