2-(4-dimethylamino-4-phenylcyclohexylidene)-1-[3-(1H-indol-3-yl)piperidine-1-yl]-ethanone → 2-(4-dimethylamino-4-phenylcyclohexyl)-1-[3-(1H-indol-3-yl)piperidine-1-yl]-ethanone

Participants

Reaction Steps

Palladium on carbon (5%, 60 mg) was added to a solution of 2-(4-dimethylamino-4-phenylcyclohexylidene)-1-[3-(1H-indol-3-yl)piperidine-1-yl]-ethanone (220 mg, 0.498 mmole) in abs. methanol (30 ml). The reaction mixture was hydrogenated for 24 hours at RT under a pressure of 3 bar. The catalyst was separated using Celite and the filtrate was concentrated by evaporation. After chromatographic separation of the residue (210 mg) on silica gel (20 g) with EE/methanol (2:1), 2-(4-dimethylamino-4-phenylcyclohexyl)-1-[3-(1H-indol-3-yl)piperidine-1-yl]-ethanone was isolated as a colourless oil in a yield of 30% (66 mg). The compound was obtained as a diastereoisomer mixture.

Provenance & Evidence