Water → Tert-butyl 4-(2-chloro-4-nitrophenyl)piperazine-1-carboxylate

HRID 32223

Reaktionsgleichung

Reaktionsgleichung von HRID 32223
[Cl:1][C:2]1[CH:3]=[C:4]([N+:9]([O-:11])=[O:10])[CH:5]=[CH:6][C:7]=1F.[C:12]([O:16][C:17]([N:19]1[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]1)=[O:18])([CH3:15])([CH3:14])[CH3:13].CN(C)C=O.O>C(Cl)(Cl)Cl>[C:12]([O:16][C:17]([N:19]1[CH2:24][CH2:23][N:22]([C:7]2[CH:6]=[CH:5][C:4]([N+:9]([O-:11])=[O:10])=[CH:3][C:2]=2[Cl:1])[CH2:21][CH2:20]1)=[O:18])([CH3:15])([CH3:13])[CH3:14]

Komponenten

6

Edukt 4

HCID 962WaterHCID 6228DimethylformamideHCID 676882-Chloro-1-fluoro-4-nitrobenzeneHCID 143452tert-Butyl piperazine-1-carboxylate

Produkt 1

HCID 18783805Tert-butyl 4-(2-chloro-4-nitrophenyl)piperazine-1-carboxylateAusbeute 64,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Reaktionsbedingungen

Temperatur
130 °C

Versuchsvorschrift

A mixture of 3-chloro-4-fluoronitrobenzene (5 g, 27.1 mmol), 1-piperazinecarboxylic acid t-butyl ester (5 g, 26.8 mmol) and dimethylformamide (10 mL) was stirred for 3 hours and 30 minutes at an external temperature of 130° C. After adding water to the air-cooled reaction mixture, extraction was performed 3 times with chloroform. The organic layers were washed with brine and dried over anhydrous magnesium sulfate. The desiccant was filtered off and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel colurn chromatography (ethyl acetate/heptane) to give 5.93 g of the title compound as a yellow solid.

Aufarbeitung

  1. customto the air-cooled reaction mixture, extraction
  2. washThe organic layers were washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationThe desiccant was filtered off
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe residue was purified by silica gel colurn chromatography (ethyl acetate/heptane)

Quellen und Nachweise

ORD-Eintrag
ord-293bca3bde1e4e4ab038e84ec05c91b5
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07425554B2

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