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

HRID 895651ノート

反応式

HRID 895651 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6569Methyl Ethyl Ketone溶媒

実験手順

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%.

後処理

  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)

出典と根拠

ORDレコード
ord-574f97bd1b76466dacd893c1db6414a7
出典データセット
uspto-grants-2005_07
特許番号
US06916822B2

反応ノート

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