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

HRID 1503832노트

반응식

HRID 1503832 반응식
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

참가 물질

7

반응물 3

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

생성물 1

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

시약·촉매·용매 3

HCID 74236Tetrabutylammonium Bromide촉매HCID 679Dimethyl Sulfoxide용매HCID 962Water용매

반응 조건

온도
125 °C

실험 절차

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+)

후처리

  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

출처 및 근거

ORD 기록
ord-2e226740e29b46618a14f04d69b57eed
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09212192B2

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