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

HRID 1503832Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1503832
Br[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[Cl:11].[N:12]1([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1.C(=O)([O-])[O-].[K+].[K+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.CS(C)=O.O>[Cl:11][C:3]1[CH:4]=[C:5]([N+:8]([O-:10])=[O:9])[CH:6]=[CH:7][C:2]=1[N:15]1[CH2:14][CH2:13][N:12]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:17][CH2:16]1

Komponenten

7

Edukt 3

HCID 11430Potassium CarbonateHCID 346671-Bromo-2-chloro-4-nitrobenzeneHCID 143452tert-Butyl piperazine-1-carboxylate

Produkt 1

HCID 18783805Tert-butyl 4-(2-chloro-4-nitrophenyl)piperazine-1-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 74236Tetrabutylammonium BromideKatalysatorHCID 679Dimethyl SulfoxideLösungsmittelHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
125 °C

Versuchsvorschrift

A mixture of 1-bromo-2-chloro-4-nitrobenzene (1 g, 4.2 mmol), tert-butyl piperazine-1-carboxylate (0.86 g, 4.6 mmol), potassium carbonate (878 mg, 6.4 mmol) and tetrabutyl ammonium bromide (137 mg, 0.42 mmol) in dimethylsulfoxide (20 mL) was heated at 125° C. for 3 hours. After cooling to ambient temperature, the mixture was diluted with water and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate, filtered, and concentrated. The residue was purified by flash chromatography on silica gel eluting with 5/1 petroleum ether/ethyl acetate to give the title compound. MS: 342 (M+H+)

Aufarbeitung

  1. temperatureAfter cooling to ambient temperature
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by flash chromatography on silica gel eluting with 5/1 petroleum ether/ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-2e226740e29b46618a14f04d69b57eed
Quelldatensatz
uspto-grants-2015_12
Patentnummer
US09212192B2

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