HCID 11676346, compound → HCID 11561090, compound

Participants

Reaction Steps

Palladium-on-charcoal (5%, 24 mg) was added to a solution of 2-[4-dimethylamino-4-(4-fluorophenyl)-cyclohexylidene]-N-(3-phenylpropyl)-acetamide (base of Example 19; 390 mg, 0.99 mmol) in abs. methanol (25 ml). The reaction mixture was hydrogenated at RT under a pressure of 2 bar for 17 h. The catalyst was separated off over Celite and the filtrate was concentrated. After separation of the residue (402 mg) by chromatography on silica gel (80 g) with EA/methanol (2:1), the less polar diastereoisomer of 2-[4-dimethylamino-4-(4-fluorophenyl)cyclohexyl]-N-(3-phenylpropyl)acetamide was isolated as a beige-coloured oil in a yield of 24% (78 mg) and the more polar diastereoisomer of 2-[4-dimethylamino-4-(4-fluorophenyl)cyclohexyl]-N-(3-phenylpropyl)acetamide was isolated as a colourless oily solid in a yield of 76% (297 mg).

Provenance & Evidence