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

HRID 241566

Reaction equation

HRID 241566 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

5

Reactant 3

HCID 6329MethylamineHCID 25604Methyl 4-nitrobutyrateHCID 1376632,5-Difluorobenzaldehyde

Product 1

HCID 67389784trans-6-(2,5-Difluorophenyl)-1-methyl-5-nitropiperidin-2-one

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

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).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux temperature overnight
  3. customAfter evaporation
  4. customthe residue was purified by column chromatography (silica gel Biotage 40M)
  5. washeluting with ethyl acetate/hexane (gradient from 40% to 60%)

Sources & evidence

ORD record
ord-1e31ca7127cd4dd08659570443fd9ba5
Source dataset
uspto-grants-2014_02
Patent number
US08653059B2

Linked notes

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