Sodium hydride → N-(2-Pyridyl)-1-[2-(4-(2-methoxyphenyl)-1-piperazinyl)ethyl]benzimidazole-2-carboxamide

HRID 476897

Reaction equation

HRID 476897 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH:7][C:8]([C:10]1[NH:11][C:12]2[CH:18]=[CH:17][CH:16]=[CH:15][C:13]=2[N:14]=1)=[O:9].[H-].[Na+].[CH3:21][O:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[N:29]1[CH2:34][CH2:33][N:32]([CH2:35][CH2:36]Cl)[CH2:31][CH2:30]1.[Cl-].[NH4+]>CS(C)=O>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH:7][C:8]([C:10]1[N:11]([CH2:36][CH2:35][N:32]2[CH2:31][CH2:30][N:29]([C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=3[O:22][CH3:21])[CH2:34][CH2:33]2)[C:12]2[CH:18]=[CH:17][CH:16]=[CH:15][C:13]=2[N:14]=1)=[O:9]

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 5956731-(2-Chloroethyl)-4-(2-methoxyphenyl)piperazineHCID 30872911H-Benzimidazole-2-carboxamide, N-2-pyridinyl-

Product 1

HCID 14371292N-(2-Pyridyl)-1-[2-(4-(2-methoxyphenyl)-1-piperazinyl)ethyl]benzimidazole-2-carboxamideYield 52.1%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

In an argon atmosphere, N-(2-pyridyl)benzimidazole-2-carboxamide (1.55 g) was dissolved in DMSO (20 ml), and 60% sodium hydride (0.28 g) was added and stirred at room temperature for 1 hr. A solution (7 ml) of 2-[4-(2-methoxyphenyl)-1-piperazinyl]ethyl chloride (1.65 g) in DMSO was added dropwise and stirred at room temperature overnight. The reaction solution was poured into an aqueous solution of ammonium chloride and extracted with chloroform, and the chloroform layer was dired. The residue obtained by distilling off the solvent was purified by column chromatography on silica gel to give the title compound (1.54 g) as amorphous solid.

Workup

  1. stirringstirred at room temperature overnight
  2. extractionextracted with chloroform
  3. customThe residue obtained
  4. distillationby distilling off the solvent
  5. customwas purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-035fea96d86f4eb0a1425042ebd72572
Source dataset
uspto-grants-1989_12
Patent number
US04886803

Linked notes

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