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Sodium Bicarbonate → 1-[2-[3-(3,4-Dichloro-phenyl)-1-(benzoyl)-pyrrolidin-3-yl]-ethyl]-4-phenylpiperidine-4-carboxylic acid amide

HRID 1682935
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HRID 1682935 반응식
CS(O[CH2:6][CH2:7][C:8]1([C:21]2[CH:26]=[CH:25][C:24]([Cl:27])=[C:23]([Cl:28])[CH:22]=2)[CH2:12][CH2:11][N:10]([C:13](=[O:20])[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:9]1)(=O)=O.Cl.[C:30]1([C:36]2([C:42]([NH2:44])=[O:43])[CH2:41][CH2:40][NH:39][CH2:38][CH2:37]2)[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.C([O-])(O)=O.[Na+]>C1COCC1>[Cl:28][C:23]1[CH:22]=[C:21]([C:8]2([CH2:7][CH2:6][N:39]3[CH2:38][CH2:37][C:36]([C:30]4[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=4)([C:42]([NH2:44])=[O:43])[CH2:41][CH2:40]3)[CH2:12][CH2:11][N:10]([C:13](=[O:20])[C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH2:9]2)[CH:26]=[CH:25][C:24]=1[Cl:27]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 516892Sodium BicarbonateHCID 30171294-Phenylpiperidine-4-carboxamide monohydrochlorideHCID 158408952-[1-Benzoyl-3-(3,4-dichloro-phenyl)-pyrrolidin-3-yl]ethyl methanesulfonate

생성물 1

HCID 442122851-[2-[3-(3,4-Dichloro-phenyl)-1-(benzoyl)-pyrrolidin-3-yl]-ethyl]-4-phenylpiperidine-4-carboxylic acid amide

시약·촉매·용매 1

HCID 8028
Tetrahydrofuran
용매

실험 절차

2-[1-Benzoyl-3-(3,4-dichloro-phenyl)-pyrrolidin-3-yl]ethyl methanesulfonate (191 mg, 0.43 mmol) was treated with the 4-phenyl-piperidine-4-carboxylic acid amide hydrochloride (144 mg, 0.599 mmol) and NaHCO3 (90 mg, 1.07 mmol, 2.5 eq.) in THF/H20 (5 mL/1 mL) at reflux for 21 hours. The solution was concentrated in vacuo and the aqueous phase was extracted with dichloromethane. The organic phase was dried over magnesium sulfate, filtered, and concentrated in vacuo. The residue was chromatographed on silica gel (30 g) with 6% methanol in dichloromethane to give 146 mg (44%).

후처리

  1. temperatureat reflux for 21 hours
  2. concentrationThe solution was concentrated in vacuo
  3. extractionthe aqueous phase was extracted with dichloromethane
  4. dry with materialThe organic phase was dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was chromatographed on silica gel (30 g) with 6% methanol in dichloromethane
  8. customto give 146 mg (44%)

출처 및 근거

ORD 기록
ord-314e4a2a6f904c1da815f189009fdd96
출처 데이터셋
uspto-grants-1997_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05635510

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