2,6-Dimethylmorpholine, cis- → 2,6-Dimethyl-4-[1-(4-nitrophenyl)-piperidin-4-yl]-morpholine

Participants

Reaction Steps

To an ice-cooled solution of 1-(4-nitro-phenyl)-piperidin-4-one (400 mg, 1.8 mmol) in acetic acid was added cis-2,6-dimethyl-morpholine (0.32 mL, 2.68 mmol) and sodium cyanoborohydride (220 mg, 3.50 mmol). The mixture was heated at reflux overnight then allowed to cool and concentrated to dryness under reduced pressure. The residue was partitioned between 5% sodium hydroxide solution and ethyl acetate. The organic phase was washed with water, brine, dried and concentrated to afford 2,6-dimethyl-4-[1-(4-nitrophenyl)-piperidin-4-yl]-morpholine (500 mg, 86%) as a yellow solid.

Provenance & Evidence