Potassium Carbonate → 1-(3-Chloro-4-nitro-phenyl)-4-ethyl-piperazine

HRID 409692

Reaktionsgleichung

Reaktionsgleichung von HRID 409692
[CH2:1]([N:3]1[CH2:8][CH2:7][NH:6][CH2:5][CH2:4]1)[CH3:2].[Cl: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>[Cl:9][C:10]1[CH:15]=[C:14]([N:6]2[CH2:7][CH2:8][N:3]([CH2:1][CH3:2])[CH2:4][CH2:5]2)[CH:13]=[CH:12][C:11]=1[N+:17]([O-:19])=[O:18]

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 750172-Chloro-4-fluoro-1-nitrobenzeneHCID 791961-Ethylpiperazine

Produkt 1

HCID 691619981-(3-Chloro-4-nitro-phenyl)-4-ethyl-piperazineAusbeute 72,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

N-Ethylpiperazine (4.3 mL, 34.3 mmol, 1.2 equiv) is added to a mixture of 2-chloro-4-fluoronitrobenzene (5 g, 28.6 mmol) and potassium carbonate (7.9 g, 57.1 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 trituration in diethyl ether to provide 5.6 g of the title compound as a yellow solid: ES-MS: 270.0 [MH]+; tR=2.90 min (system 1).

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 trituration in diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-3e7fc2a34c1e49d3b9f834f4b314766b
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08759517B2

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