Water → 1-[2-[3-(3,4-Dichloro-phenyl)-1-(2,4-dimethoxy-benzoyl)-pyrrolidin-3-yl]-ethyl]-4-phenyl-piperidine-4-carboxylic acid amide

HRID 265915노트

반응식

HRID 265915 반응식
[CH3:1][O:2][C:3]1[CH:30]=[C:29]([O:31][CH3:32])[CH:28]=[CH:27][C:4]=1[C:5]([N:7]1[CH2:11][CH2:10][C:9]([CH2:20][CH2:21]CS([O-])(=O)=O)([C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[C:14]([Cl:19])[CH:13]=2)[CH2:8]1)=[O:6].Cl.[C:34]1([C:40]2([C:46]([NH2:48])=[O:47])[CH2:45][CH2:44][NH:43][CH2:42][CH2:41]2)[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1.C(=O)([O-])[O-].[K+].[K+].O>C1COCC1>[Cl:19][C:14]1[CH:13]=[C:12]([C:9]2([CH2:20][CH2:21][N:43]3[CH2:42][CH2:41][C:40]([C:34]4[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=4)([C:46]([NH2:48])=[O:47])[CH2:45][CH2:44]3)[CH2:10][CH2:11][N:7]([C:5](=[O:6])[C:4]3[CH:27]=[CH:28][C:29]([O:31][CH3:32])=[CH:30][C:3]=3[O:2][CH3:1])[CH2:8]2)[CH:17]=[CH:16][C:15]=1[Cl:18]

참가 물질

6

반응물 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 30171294-Phenylpiperidine-4-carboxamide monohydrochlorideHCID 867509052-[1-(2,4-Dimethoxy-benzoyl)-3-(3,4-dichloro-phenyl)-pyrrolidin-3-yl]-ethyl-methanesulfonate

생성물 1

HCID 442122841-[2-[3-(3,4-Dichloro-phenyl)-1-(2,4-dimethoxy-benzoyl)-pyrrolidin-3-yl]-ethyl]-4-phenyl-piperidine-4-carboxylic acid amide수율 36.4%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

2-[1-(2,4-Dimethoxy-benzoyl)-3-(3,4-dichloro-phenyl)-pyrrolidin-3-yl]-ethyl-methanesulfonate (343 mg, 0.68 mmol) was dissolved in THF (8 mL) and the 4-phenyl-piperidine-4-carboxylic acid amide hydrochloride (170 mg, 0.71 mmol, 1.04 eq.), potassium carbonate (200 mg, 1.45 mmol, 2.1 eq.), and water (2 mL) were added and the solution was heated at reflux for 16 hours. The solution was concentrated in vacuo and the aqueous phase was extracted with dichloromethane, dried over magnesium sulfate, filtered, and concentrated in vacuo. The residue was chromatographed on silica gel (40 g) with a gradient of ethyl acetate to 6% methanol in dichloromethane to give 151 mg (36%) of the title compound.

후처리

  1. temperaturethe solution was heated
  2. temperatureat reflux for 16 hours
  3. concentrationThe solution was concentrated in vacuo
  4. extractionthe aqueous phase was extracted with dichloromethane
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was chromatographed on silica gel (40 g) with a gradient of ethyl acetate to 6% methanol in dichloromethane

출처 및 근거

ORD 기록
ord-7bb48001271a4aa088cae18790e56ed0
출처 데이터셋
uspto-grants-1997_07
특허 번호
US05648366

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