Triethylamine → 4-(4-Fluorophenyl)-piperazine-1-carboxylic acid 4-nitrophenyl ester

HRID 2262470노트

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HRID 2262470 반응식
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.C(N(CC)CC)C.Cl[C:22]([O:24][C:25]1[CH:30]=[CH:29][C:28]([N+:31]([O-:33])=[O:32])=[CH:27][CH:26]=1)=[O:23]>C1COCC1>[N+:31]([C:28]1[CH:27]=[CH:26][C:25]([O:24][C:22]([N:11]2[CH2:12][CH2:13][N:8]([C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=3)[CH2:9][CH2:10]2)=[O:23])=[CH:30][CH:29]=1)([O-:33])=[O:32]

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 752601-(4-Fluorophenyl)piperazineHCID 821294-Nitrophenyl chloroformate

생성물 1

HCID 595944824-(4-Fluorophenyl)-piperazine-1-carboxylic acid 4-nitrophenyl ester수율 67.6%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

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온도
0 °C

실험 절차

1-(4-Fluoro-phenyl)-piperazine (12.2 g, 67.7 mmol) and triethylamine (4.63 mL, 67.7 mmol) were dissolved in anhydrous THF (150 mL) under nitrogen and the reaction mixture was cooled to 0° C. 4-Nitrophenyl chloroformate (13.4 g, 67.7 mmol) dissolved in anhydrous THF (150 mL) at 0° C. was added and the reaction mixture was stirred at room temperature overnight. The solvent was removed in vacuo and the residue suspended between water and EtOAc. The aqueous layer was extracted with two further portions of EtOAc, the organic layers were combined, dried (MgSO4), dried in vacuo and then recrystallised from toluene (50 mL)/hexane (60 mL) to give 4-(4-fluorophenyl)-piperazine-1-carboxylic acid 4-nitrophenyl ester (15.8 g, 67%) as fine yellow needles.

후처리

  1. additionwas added
  2. customThe solvent was removed in vacuo
  3. extractionThe aqueous layer was extracted with two further portions of EtOAc
  4. dry with materialdried (MgSO4)
  5. customdried in vacuo
  6. customrecrystallised from toluene (50 mL)/hexane (60 mL)

출처 및 근거

ORD 기록
ord-97e67a0b8d264d1c9a18424c2126d1a0
출처 데이터셋
uspto-grants-2010_12
특허 번호
US07851471B2

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