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

HRID 895651Notes

Reaction equation

HRID 895651 reaction equation
[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]

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

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%.

Workup

  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)

Sources & evidence

ORD record
ord-574f97bd1b76466dacd893c1db6414a7
Source dataset
uspto-grants-2005_07
Patent number
US06916822B2

Reaction notes

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