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

HRID 32223

반응식

HRID 32223 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

HCID 18783805Tert-butyl 4-(2-chloro-4-nitrophenyl)piperazine-1-carboxylate수율 64.7%

시약·촉매·용매 1

HCID 6212Chloroform용매

반응 조건

온도
130 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-293bca3bde1e4e4ab038e84ec05c91b5
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07425554B2

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