Water → 5-(4-Methylpiperazin-1-yl)-2-nitroaniline

HRID 884406

Reaktionsgleichung

Reaktionsgleichung von HRID 884406
Cl[C:2]1[CH:3]=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([NH2:8])[CH:7]=1.[CH3:12][N:13]1[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[CH3:12][N:13]1[CH2:18][CH2:17][N:16]([C:2]2[CH:3]=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([NH2:8])[CH:7]=2)[CH2:15][CH2:14]1

Komponenten

6

Edukt 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 531671-MethylpiperazineHCID 742185-Chloro-2-nitroaniline

Produkt 1

HCID 27600345-(4-Methylpiperazin-1-yl)-2-nitroanilineAusbeute 54,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

A mixture of 5-chloro-2-nitrophenylamine (2.5 g, 14 mmol), 1-methylpiperizine (3.2 mL, 30 mmol), and potassium carbonate (K2CO3) (2.0 g, 14 mmol) in dimethylformamide (DMF) (20 mL) was stirred at 120° C. for 18 h. The reaction mixture was cooled to room temperature and poured into water (150 mL). The precipitated crude product was collected by filtration, dried in vacuo, and purified by recrystallization from ethyl acetate (EtOAc) (75 mL) to yield yellow-green crystals (1.8 g, 54%). See, J. Med. Chem., 39:997 (1996).

Aufarbeitung

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customThe precipitated crude product
  3. filtrationwas collected by filtration
  4. customdried in vacuo
  5. custompurified by recrystallization from ethyl acetate (EtOAc) (75 mL)

Quellen und Nachweise

ORD-Eintrag
ord-c3239f7950ef4095aac97de3572ff317
Quelldatensatz
uspto-grants-2012_08
Patentnummer
US08242115B2

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