Methylamine → trans-6-(2,5-Difluorophenyl)-1-methyl-5-nitropiperidin-2-one

Reaction equation

[F:1][C:2]1[CH:9]=[CH:8][C:7]([F:10])=[CH:6][C:3]=1[CH:4]=O.[N+:11]([CH2:14][CH2:15][CH2:16][C:17]([O:19]C)=O)([O-:13])=[O:12].[CH3:21][NH2:22]>C(O)C>[F:1][C:2]1[CH:9]=[CH:8][C:7]([F:10])=[CH:6][C:3]=1[C@@H:4]1[N:22]([CH3:21])[C:17](=[O:19])[CH2:16][CH2:15][C@H:14]1[N+:11]([O-:13])=[O:12]

Participants

Procedure

To a solution of 2,5-difluorobenzaldehyde (0.765 mL, 7.04 mmol) in ethanol (15 mL) were added methyl 4-nitrobutyrate (0.901 mL, 7.04 mmol) and methylamine (7.04 mL, 14.07 mmol). The mixture was heated at reflux temperature overnight. After evaporation, the residue was purified by column chromatography (silica gel Biotage 40M) eluting with ethyl acetate/hexane (gradient from 40% to 60%) to give the title compound as the racemic trans isomer. LC-MS: 271.05 (M+1).