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

HRID 241566

Reaktionsgleichung

Reaktionsgleichung von HRID 241566
[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]

Komponenten

5

Edukt 3

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  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%)

Quellen und Nachweise

ORD-Eintrag
ord-1e31ca7127cd4dd08659570443fd9ba5
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08653059B2

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