Water → tert-Butyl 4-(3-aminophenyl)piperazine-1-carboxylate

HRID 1633593

반응식

HRID 1633593 반응식
[N:1]1([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.F[C:15]1[CH:16]=[C:17]([N+:21]([O-])=O)[CH:18]=[CH:19][CH:20]=1.O>CN1C(=O)CCC1>[C:10]([O:9][C:7]([N:1]1[CH2:6][CH2:5][N:4]([C:15]2[CH:16]=[C:17]([CH:18]=[CH:19][CH:20]=2)[NH2:21])[CH2:3][CH2:2]1)=[O:8])([CH3:13])([CH3:12])[CH3:11]

참가 물질

5

반응물 3

HCID 962WaterHCID 98231-Fluoro-3-nitrobenzeneHCID 143452tert-Butyl piperazine-1-carboxylate

생성물 1

HCID 22330182tert-Butyl 4-(3-aminophenyl)piperazine-1-carboxylate

시약·촉매·용매 1

HCID 13387N-methyl-2-pyrrolidone용매

반응 조건

온도
120 °C

실험 절차

A mixture of tert-butyl 1-piperazinecarboxylate (4 g, 21.5 mmol) and 3-fluoronitrobenzene (2.3 ml, 21.5 mmol) in anhydrous NMP (5 ml) was heated to 120° C. for 3 days. After cooling water (25 ml) was added and the mixture was extracted with ethyl acetate (2×10 ml). The organic extract was dried over sodium sulfate and the solvent was removed under reduced pressure. The residue was purified by column-chromatography using successively petroleum ether and a mixture of ethyl acetate and petroleum ether (1:1 v/v) as the eluents. Yield of t-butyl 4-(3-nitrophenyl)-1-piperazinecarboxylate: 1.34 g (20%). This intermediate was quantitatively hydrogenated to 2g in ethanol at ambient pressure using Pd (5% on activated carbon) as the catalyst.

후처리

  1. additionwas added
  2. extractionthe mixture was extracted with ethyl acetate (2×10 ml)
  3. extractionThe organic extract
  4. dry with materialwas dried over sodium sulfate
  5. customthe solvent was removed under reduced pressure
  6. customThe residue was purified by column-chromatography
  7. additiona mixture of ethyl acetate and petroleum ether (1:1 v/v) as the eluents

출처 및 근거

ORD 기록
ord-c4fbda0980894972b8318a8c05c224dc
출처 데이터셋
uspto-grants-2003_01
특허 번호
US06503925B1

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