Hexylamine → 4-Ethyl-N-hexyl-4-(3-nitrophenyl)piperidine

Participants

Reaction Steps

To a solution of 3-ethyl-5-((methylsulfonyl)oxy)-3-(3-nitrophenyl)pentyl methanesulfonate (Preparation 62, 850 mg, 2.1 mmol) in toluene (6 ml) under an atmosphere of nitrogen was added hexylamine (1.66 ml, 12.6 mmol). The reaction mixture was heated under reflux for 16 h, then it was concentrated in vacuo to give the crude product. This was purified by silica (25 g) column chromatography eluting with ethyl acetate:hexane:0.880 ammonia (49:50:1) to give the title compound as a clear oil (335 mg, 50%).

Provenance & Evidence