Benzaldehyde → 58373-38-9

Participants

Reaction Conditions

Reaction Steps

A solution of methyl 4-nitrobutyrate (23g) and benzaldehyde (16ml) in acetic acid (39ml) containing ammonium acetate (12.12g) was heated at reflux under nitrogen for 2h. The reaction mixture was cooled to 5° C., whereby a pale-yellow solid crystallised. This was isolated by filtration, then dissolved in dichloromethane, washed cautiously with saturated aqueous sodium bicarbonate solution (2×), then dried (MgSO4) and concentrated to leave a yellow solid. Recrystallisation from ethyl acetate provided 5-nitro-2-oxo-6-phenylpiperidine (12.5g) as a crystalline, white solid. 1H NMR (CDCl3) δ7.46-7.26 (m), 6.0 (br s), 5.24 (dd, J=1.4, 7.0Hz), 4.70 (m), 2.70-2.50 (m), 2.38-2.24 (m).

Provenance & Evidence