HCID 66783290, compound → HCID 24955779, compound

Participants

Reaction Steps

The free base from Example 33 (210 mg, 0.567 mmol) was dissolved in methanol (35 ml), and palladium on charcoal (5 per cent strength; 90 mg) was added. The reaction mixture was hydrogenated under 3 bar for 5 h. The catalyst was separated off over Celite and the filtrate was concentrated. The solid residue (185 mg) was separated by chromatography [silica gel 60 (40 g); ethyl acetate/methanol 10:1 (250 ml), ethyl acetate/methanol 4:1 (250 ml)]. 1-Benzyl-4-(3-cyclopropyl-1H-indol-2-yl)-N,N-dimethylcyclohexanamin (more polar diastereoisomer) was obtained in a yield of 50% (105 mg) with a melting point of 65-70° C. The less polar diastereoisomer was isolated in a yield of 26% (54 mg) together with by-products. This fraction was purified again by chromatography [silica gel 60 (20 g); trichloromethane/methanol 40:1 (250 ml)]. The less polar diastereoisomer was obtained by this procedure in a yield of 43 mg (20%) with traces of an impurity and was employed in this form for the citrate preparation.

Provenance & Evidence