Triethylamine → (+)-(3,5-Dimethylbenzoyl)-3-(3,4-dichlorophenyl)piperazine

HRID 362538

반응식

HRID 362538 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]2[CH2:14][NH:13][CH2:12][CH2:11][NH:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8].[CH3:15][C:16]1[CH:17]=[C:18]([CH:22]=[C:23]([CH3:25])[CH:24]=1)[C:19](O)=[O:20].O.ON1C2C=CC=CC=2N=N1.CCN(CC)CC>C(Cl)Cl>[CH3:15][C:16]1[CH:17]=[C:18]([CH:22]=[C:23]([CH3:25])[CH:24]=1)[C:19]([N:13]1[CH2:12][CH2:11][NH:10][CH:9]([C:4]2[CH:5]=[CH:6][C:7]([Cl:8])=[C:2]([Cl:1])[CH:3]=2)[CH2:14]1)=[O:20]

참가 물질

6

반응물 4

HCID 8471TriethylamineHCID 103563,5-Dimethylbenzoic acidHCID 27960291-Hydroxybenzotriazole hydrateHCID 42313562-(3,4-Dichlorophenyl)piperazine

생성물 1

HCID 10292159(+)-(3,5-Dimethylbenzoyl)-3-(3,4-dichlorophenyl)piperazine수율 57.8%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

To a cooled solution of CH2Cl2 (600 mL) containing 2-(3,4-dichlorophenyl)piperazine (6.934 g, 30 mmol), 3,5-dimethylbenzoic acid (4.55 g, 30 mmol), and N-hydroxybenzotriazole monohydrate (4.05 g, 30 mmol) at -20° C. were added Et3N (4.2 mL, 30 mmol) and N,N-dimethylaminopropylethylcarbodimide (DEC) (5.86 g, 30 mmol) under nitrogen. The reaction was kept at -20° C. for an hour and gradually warmed to RT overnight. After stirring 22 hours, the reaction was complete and CH2Cl2 (200 mL) was added. The organic solution was washed with brine (150 mL, 3×), dried over MgSO4 , filtered and concentrated under vacuum to give 8.2 g of crude product. The product was crystallized from CH2Cl2 /Hexane to give a light yellow solid (6.3 g, 17.34 mmol, 57.8%), m.p.139°-141° C.; FAB MS [M+1]+ 35 Cl 363.1.

후처리

  1. waitThe reaction was kept at -20° C. for an hour
  2. washThe organic solution was washed with brine (150 mL, 3×)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum
  6. customto give 8.2 g of crude product
  7. customThe product was crystallized from CH2Cl2 /Hexane

출처 및 근거

ORD 기록
ord-e9ebd2f29c474f09a017160676750579
출처 데이터셋
uspto-grants-1999_02
특허 번호
US05869488

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