Ethanol → 4-(3-aminophenyl)-4-ethyl-N-hexylpiperidine

Participants

Reaction Steps

To a solution of 4-ethyl-N-hexyl-4-(3-nitrophenyl)piperidine (Preparation 63, 335 mg, 1.05 mmol) in 9:1 ethanol:water (41 ml) was added iron powder (530 mg, 9.45 mmol) followed by calcium chloride (58 mg, 0.53 mmol). The reaction mixture was heated under reflux for 2 h, then the mixture was allowed to cool. The mixture was filtered and the filtrate was concentrated in vacuo. The residue was partitioned between dichloromethane (20 ml) and water (20 ml). The phases were separated and the organic extract was dried (MgSO4), filtered and concentrated in vacuo to give the crude product. This was purified by silica (10 g) column chromatography eluting with methanol:dichloromethane:0.880 ammonia (10:89:1) to give the title compound as a brown oil (103 mg, 34%).

Provenance & Evidence