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Benzoyl chloride → [3-(3,4-Dichlorophenyl)-3-(3-hydroxy-propyl)-piperidin-1-yl]-phenyl-methanone

HRID 394547
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인쇄 미리보기

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HRID 394547 반응식
C(N(C(C)C)CC)(C)C.CC1(C)C2CC[C@@]1(CS([O:23][CH2:24][CH2:25][CH2:26][C@@:27]1([C:33]3[CH:38]=[CH:37][C:36]([Cl:39])=[C:35]([Cl:40])[CH:34]=3)[CH2:32][CH2:31][CH2:30][NH:29][CH2:28]1)(=O)=O)C(=O)C2.[C:42]1([C:48](Cl)=[O:49])[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1>C(Cl)Cl>[Cl:40][C:35]1[CH:34]=[C:33]([C:27]2([CH2:26][CH2:25][CH2:24][OH:23])[CH2:32][CH2:31][CH2:30][N:29]([C:48]([C:42]3[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=3)=[O:49])[CH2:28]2)[CH:38]=[CH:37][C:36]=1[Cl:39]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 7412Benzoyl chlorideHCID 81531DiisopropylethylamineHCID 131724007(R)-3-[3-(3,4-Dichlorophenyl)-piperidin-3-yl]-propan-1-ol(1s)-7,7-dimethyl-2-oxobicyclo[2,2,1]heptane-1-methanesulfonate

생성물 1

HCID 22741724[3-(3,4-Dichlorophenyl)-3-(3-hydroxy-propyl)-piperidin-1-yl]-phenyl-methanone수율 89.8%

시약·촉매·용매 1

HCID 6344
Dichloromethane
용매
2회

실험 절차

Diisopropylethylamine(5.7 mL, 3.27 mmol, 5.0 eq) was added to a mixture of camphorsulfonate salt (9) (3.4 g, 6.53 mmol) in CH2Cl2 (21 mL, 0.3 M) and followed by dropwise addition of PhCOCl (0.83 mL, 7.19 mmol, 1.1 eq). The solution was stirred at room temperature for 1 hour. The reacting mixture was diluted with CH2Cl2 (200 mL) and washed with brine, 1 M KHSO4, and saturated NaHCO3 then dried over MgSO4. The concentrated crude oil was purified by flash chromatography (CH2Cl2-MeOH/95:5) to give white solid (2.30 g, 89.8%).

후처리

  1. washwashed with brine, 1 M KHSO4, and saturated NaHCO3
  2. dry with materialthen dried over MgSO4
  3. concentrationThe concentrated crude oil
  4. customwas purified by flash chromatography (CH2Cl2-MeOH/95:5)

출처 및 근거

ORD 기록
ord-ebda47b7e3ba4ce1b5ae61b0d6bbbf8d
출처 데이터셋
uspto-grants-2003_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06602886B2

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