rac-1-[1-(3-Nitro-phenyl)-ethyl]-piperidine-4-carboxylic acid cyclohexylamide → rac-1-[1-(3-Amino-phenyl)-ethyl]-piperidine-4-carboxylic acid cyclohexylamide

Participants

Reaction Steps

A solution of rac-1-[1-(3-nitro-phenyl)-ethyl]-piperidine-4-carboxylic acid cyclohexylamide (375 mg, 1.04 mmol) in MeOH (15 mL) is treated with anhydrous stannous chloride (908 mg, 4.7 mmol). The mixture is heated at reflux overnight. The mixture is let to cool to RT and MeOH is evaporated under reduced pressure. Water (25 mL) is added to the residue, followed by saturated NaHCO3 solution (25 mL). The mixture is extracted twice with DCM (25 mL), the organic phases are washed with water (25 mL), brine (25 mL) and dried over MgSO4. The crude product (0.35 g, 99%) is isolated after evaporation under reduced pressure as a colorless oil: LC-MS A: tR=0.51 min; [M+H]+=330.31.

Provenance & Evidence