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Sodium Bicarbonate → 1-[2-[1-Benzoyl-3-(3,4-dichloro-phenyl)-pyrrolidin-3-yl]-ethyl]-4-phenyl-piperidine-4-carboxylic acid methyl ester

HRID 1682946
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HRID 1682946 반응식
Cl.[CH3:2][O:3][C:4]([C:6]1([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:11][CH2:10][NH:9][CH2:8][CH2:7]1)=[O:5].[C:18]([N:26]1[CH2:30][CH2:29][C:28]([CH2:39][CH2:40]CS([O-])(=O)=O)([C:31]2[CH:36]=[CH:35][C:34]([Cl:37])=[C:33]([Cl:38])[CH:32]=2)[CH2:27]1)(=[O:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C(=O)(O)[O-].[Na+]>C1COCC1.O.C(OCC)(=O)C>[CH3:2][O:3][C:4]([C:6]1([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:7][CH2:8][N:9]([CH2:40][CH2:39][C:28]2([C:31]3[CH:36]=[CH:35][C:34]([Cl:37])=[C:33]([Cl:38])[CH:32]=3)[CH2:29][CH2:30][N:26]([C:18](=[O:25])[C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH2:27]2)[CH2:10][CH2:11]1)=[O:5]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

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반응물 3

HCID 516892Sodium BicarbonateHCID 3019446Methyl 4-phenylpiperidine-4-carboxylate hydrochlorideHCID 867509072-[1-Benzoyl-3-(3,4-dichloro-phenyl)-pyrrolidin-3-yl]-ethylmethanesulfonate

생성물 1

HCID 539315011-[2-[1-Benzoyl-3-(3,4-dichloro-phenyl)-pyrrolidin-3-yl]-ethyl]-4-phenyl-piperidine-4-carboxylic acid methyl ester수율 31.1%

시약·촉매·용매 2

HCID 8857
Ethyl Acetate
용매
HCID 21881883Oxolane--water (1/1)용매

실험 절차

4-Phenyl-piperidine-4-carboxylic acid methyl ester hydrochloride (0.4143 g, 1.62 mmol) and 2-[1-benzoyl-3-(3,4-dichloro-phenyl)-pyrrolidin-3-yl]-ethylmethanesulfonate (0.7165 g, 1.62 mmol) were dissolved in THF/H2O (20 mL/4 mL) and treated with sodium bicarbonate (0.2592 g, 3.24 mmol) at reflux for 16 hours. The solution was diluted with ethyl acetate and the aqueous phase was extracted with dichloromethane. The combined organic phases were dried over magnesium sulfate, filtered, and concentrated in vacuo. The residue was chromatographed on silica gel with 1% methanol in dichloromethane to give 0.2850 g (31%) of the title compound.

후처리

  1. temperatureat reflux for 16 hours
  2. extractionthe aqueous phase was extracted with dichloromethane
  3. dry with materialThe combined organic phases were dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was chromatographed on silica gel with 1% methanol in dichloromethane

출처 및 근거

ORD 기록
ord-fd16d23a0c714c2db00c1a729e6a6a0d
출처 데이터셋
uspto-grants-1997_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05635510

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