Potassium Carbonate → 1-(3-Chloro-4-nitrophenyl)-4-methylpiperazine

HRID 1919692

Reaktionsgleichung

Reaktionsgleichung von HRID 1919692
[Cl:1][C:2]1[CH:7]=[C:6](F)[CH:5]=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].[CH3:12][N:13]1[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.O>[Cl:1][C:2]1[CH:7]=[C:6]([N:16]2[CH2:17][CH2:18][N:13]([CH3:12])[CH2:14][CH2:15]2)[CH:5]=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10]

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 531671-MethylpiperazineHCID 750172-Chloro-4-fluoro-1-nitrobenzene

Produkt 1

HCID 231396071-(3-Chloro-4-nitrophenyl)-4-methylpiperazine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

2-chloro-4-fluoronitrobenzene (1.0 eq, 1 g, 5.7 mmol), N-methyl piperazine (1.2 eq, 1.18 g, 6.84 mmol), potassium carbonate (2.0 eq, 1.6 g, 11.6 mmol) were stirred at 100° C. in DMF for 3 hours. The mixture was cooled down and diluted with water. The material was extracted with ethyl acetate. The organic layer was washed with brine, dried over Na2SO4 and the solvent evaporated in vacuo. After trituration in diethylether and filtration, 1-(3-chloro-4-nitrophenyl)-4-methylpiperazine was isolated as a solid (0.9 g, 62%). LCMS (ES): m/z 256 [M+1]+. This material was suspended in MeOH (20 ml) with Raney Nickel (0.2 g) and stirred under hydrogen atmosphere overnight. The catalyst was filtered off through celite. Evaporation of the solvents provided 2-chloro-4-(4-methylpiperazin-1-yl)aniline as a dark brown oil (0.68 g, 86%). LCMS (ES): m/z 226 [M+1]+.

Aufarbeitung

  1. temperatureThe mixture was cooled down
  2. extractionThe material was extracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. customthe solvent evaporated in vacuo
  6. filtrationAfter trituration in diethylether and filtration

Quellen und Nachweise

ORD-Eintrag
ord-147d905ba43d462ba6ab47f10fe2c133
Quelldatensatz
uspto-grants-2012_05
Patentnummer
US08168651B2

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