Potassium Carbonate → 1-Ethyl-4-(3-fluoro-4-nitro-phenyl)-piperazine

HRID 409694Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 409694
[CH2:1]([N:3]1[CH2:8][CH2:7][NH:6][CH2:5][CH2:4]1)[CH3:2].[F:9][C:10]1[CH:15]=[C:14](F)[CH:13]=[CH:12][C:11]=1[N+:17]([O-:19])=[O:18].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.O>[CH2:1]([N:3]1[CH2:8][CH2:7][N:6]([C:14]2[CH:13]=[CH:12][C:11]([N+:17]([O-:19])=[O:18])=[C:10]([F:9])[CH:15]=2)[CH2:5][CH2:4]1)[CH3:2]

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 679672,4-DifluoronitrobenzeneHCID 791961-Ethylpiperazine

Produkt 1

HCID 691789001-Ethyl-4-(3-fluoro-4-nitro-phenyl)-piperazine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

N-Ethylpiperazine (4.8 mL, 37.7 mmol, 1.2 equiv) is added to a mixture of 2,4-difluoronitrobenzene (5 g, 31.4 mmol) and potassium carbonate (8.7 g, 62.9 mmol, 2 equiv) in DMF (50 mL). The reaction mixture is stirred at 100° C. for 6 h, allowed to cool to RT, diluted with H2O and extracted with EtOAc. The organic phase is washed with brine, dried (Na2SO4), filtered and concentrated. The residue is purified by silica gel column chromatography (DCM/MeOH+1% NH3aq, 95:5) to provide the title compound as a yellow oil: ES-MS: 254.1 [MH]+; TLC: Rf=0.67 (DCM/MeOH+1% NH3aq, 95:5).

Aufarbeitung

  1. temperatureto cool to RT
  2. extractionextracted with EtOAc
  3. washThe organic phase is washed with brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue is purified by silica gel column chromatography (DCM/MeOH+1% NH3aq, 95:5)

Quellen und Nachweise

ORD-Eintrag
ord-99d21ec3fa364b798f4f19a5f0c46cc9
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08759517B2

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