Potassium Carbonate → 1-(2-Fluoro-4-nitrophenyl)piperidin-4-one

HRID 895124Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 895124
[NH:1]1[CH2:6][CH2:5][C:4](=[O:7])[CH2:3][CH2:2]1.C(=O)([O-])[O-].[K+].[K+].[F:14][C:15]1[CH:16]=[C:17]([N+:22]([O-:24])=[O:23])[CH:18]=[CH:19][C:20]=1F>CN(C=O)C>[F:14][C:15]1[CH:16]=[C:17]([N+:22]([O-:24])=[O:23])[CH:18]=[CH:19][C:20]=1[N:1]1[CH2:6][CH2:5][C:4](=[O:7])[CH2:3][CH2:2]1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 337214-PiperidoneHCID 1230531,2-Difluoro-4-nitrobenzene

Produkt 1

HCID 37637811-(2-Fluoro-4-nitrophenyl)piperidin-4-oneAusbeute 50 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

To a stirred solution of 4-piperidinone (9.7 g, 63 mmol) and dry potassium carbonate (21.6 g, 157 mmol) in DMF (30 ml) was added 3,4-difluoro nitrobenzene (10 g, 63 mmol) and reaction mixture was heated to 90° C. for 3 h. The reaction mixture was poured into ice-water arid extracted with ethyl acetate (100 ml×2). Combined organic layer was washed with water followed by brine and dried over sodium sulfate. Evaporation of volatiles and purification of the resulting residue by silica gel column chromatography (ethyl acetate/pet. ether, 1:4) yielded the title compound (7 g, 50%).

Aufarbeitung

  1. extractionextracted with ethyl acetate (100 ml×2)
  2. washCombined organic layer was washed with water
  3. dry with materialdried over sodium sulfate
  4. customEvaporation of volatiles and purification of the resulting residue by silica gel column chromatography (ethyl acetate/pet. ether, 1:4)

Quellen und Nachweise

ORD-Eintrag
ord-27f45f036ce040d89472ebef5a934e0e
Quelldatensatz
uspto-grants-2005_07
Patentnummer
US06914058B2

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