Water → 1-[3-[2-(4-Diethylcarbamoylbenzyl)phenoxy]propyl]-4-(1,3-dihydro-2H-benzimidazol-2-on-1-yl)piperidine

HRID 895651노트

반응식

HRID 895651 반응식
[N:1]1([CH:11]2[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]2)[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[NH:3][C:2]1=[O:10].Br[CH2:18][CH2:19][CH2:20][O:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[CH2:28][C:29]1[CH:34]=[CH:33][C:32]([C:35](=[O:41])[N:36]([CH2:39][CH3:40])[CH2:37][CH3:38])=[CH:31][CH:30]=1.C(N(CC)CC)C.O>C(C(C)=O)C>[CH2:39]([N:36]([CH2:37][CH3:38])[C:35]([C:32]1[CH:33]=[CH:34][C:29]([CH2:28][C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=2[O:21][CH2:20][CH2:19][CH2:18][N:14]2[CH2:15][CH2:16][CH:11]([N:1]3[C:5]4[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=4[NH:3][C:2]3=[O:10])[CH2:12][CH2:13]2)=[CH:30][CH:31]=1)=[O:41])[CH3:40]

참가 물질

6

반응물 4

HCID 962WaterHCID 8471TriethylamineHCID 886381,3-Dihydro-1-(4-piperidinyl)-2H-benzimidazol-2-oneHCID 120503951-Bromo-3-[2-(4-diethylcarbamoylbenzyl)phenoxy]propane

생성물 1

HCID 120503961-[3-[2-(4-Diethylcarbamoylbenzyl)phenoxy]propyl]-4-(1,3-dihydro-2H-benzimidazol-2-on-1-yl)piperidine수율 41%

시약·촉매·용매 1

HCID 6569Methyl Ethyl Ketone용매

실험 절차

4-(1,3-Dihydro-2H-benzimidazol-2-on-1-yl)piperidine (49 mg) was dissolved in methyl ethyl ketone (1.8 ml), added with the 1-bromo-3-[2-(4-diethylcarbamoylbenzyl)-phenoxy]propane (91 mg) obtained in Reference Example 1 and triethylamine (47 μl) and stirred at room temperature for 17 hours. The reaction mixture was added with water (2 ml) and extracted twice with ethyl acetate (2 ml). The organic layer was dried over anhydrous magnesium sulfate, and then the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (elution solvent: dichloromethane:methanol=20:1) to obtain 49.7 mg of the title compound. Yield: 41%.

후처리

  1. extractionextracted twice with ethyl acetate (2 ml)
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. customthe solvent was evaporated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (elution solvent: dichloromethane:methanol=20:1)

출처 및 근거

ORD 기록
ord-574f97bd1b76466dacd893c1db6414a7
출처 데이터셋
uspto-grants-2005_07
특허 번호
US06916822B2

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