HCID 66782806, compound → HCID 24953645, compound

Participants

Reaction Steps

(±)-[1-Benzyl-4-(3-methyl-5-trifluoromethyl-1H-indol-2-yl)cyclohex-3-enyl]-dimethylamine (220 mg, 0.53 mmol) was dissolved in methanol (50 ml), while heating, and Pd/C (5%, 100 mg) was added under argon. Hydrogenation was carried out at 40° C. under 3 bar for 4 h. The catalyst was then filtered off with suction over Celite and the filtrate was concentrated. The solid colourless residue was separated by chromatography [silica gel 60 (30 g); ethyl acetate/methanol (20:1; 500 ml); (4:1; 300 ml); (2:1; 300 ml)]. N-[1-Benzyl-4-(3-methyl-5-trifluoromethyl-1H-indol-2-yl)cyclohexyl]-N,N-dimethylamine (less polar diastereoisomer) was isolated in a yield of 46 mg (21%) as a colourless solid with a melting point of 180-210° C. The polar diastereoisomer was obtained in a yield of 152 mg (69%) as a colourless solid with a melting point of 166-174° C.

Provenance & Evidence