Acetic Acid → trans-6-(2,5-Difluorophenyl)-1-benzyl-5-nitropiperidin-2-one

HRID 241573

Reaktionsgleichung

Reaktionsgleichung von HRID 241573
[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].[CH2:21]([NH2:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C([O-])(=O)C.[Na+].C(O)(=O)C>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:28]([CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:17](=[O:19])[CH2:16][CH2:15][C@H:14]1[N+:11]([O-:13])=[O:12]

Komponenten

7

Edukt 5

HCID 176Acetic AcidHCID 7504BenzylamineHCID 25604Methyl 4-nitrobutyrateHCID 1376632,5-DifluorobenzaldehydeHCID 517045Sodium Acetate

Produkt 1

HCID 67388890trans-6-(2,5-Difluorophenyl)-1-benzyl-5-nitropiperidin-2-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

To a solution of 2,5-difluorobenzaldehyde (1.09 g, 7.67 mmol) in ethanol (20 mL) were added methyl 4-nitrobutyrate (1.13 g, 7.04 mmol), benzylamine (0.98 mL, 7.67 mmol), sodium acetate (1.26 g, 15.3 mmol) and acetic acid (0.88 mL, 15.4 mmol). The mixture was stirred at rt for 12 h and then 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 3% to 50%) to give the title compound as the racemic trans isomer. LC-MS: 347.1 (M+1).

Aufarbeitung

  1. temperatureheated
  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 3% to 50%)

Quellen und Nachweise

ORD-Eintrag
ord-9c81f34126db454a9c58bf2b4af6f2ab
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08653059B2

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