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

HRID 241566

反応式

HRID 241566 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

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).

後処理

  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%)

出典と根拠

ORDレコード
ord-1e31ca7127cd4dd08659570443fd9ba5
出典データセット
uspto-grants-2014_02
特許番号
US08653059B2

関連ノート

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