Sodium hydride → N-(2-pyridyl)-1-[2-(4-(3,4-dimethoxybenzoyl)-1-piperazinyl)ethyl]benzimidazole-2-carboxamide

HRID 476899

Reaction equation

HRID 476899 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:24]=[C:25]([CH:37]=[CH:38][C:39]=1[O:40][CH3:41])[C:26]([N:28]1[CH2:33][CH2:32][N:31]([CH2:34][CH2:35]Cl)[CH2:30][CH2:29]1)=[O:27].[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]([CH2:35][CH2:34][N:31]2[CH2:32][CH2:33][N:28]([C:26](=[O:27])[C:25]3[CH:37]=[CH:38][C:39]([O:40][CH3:41])=[C:23]([O:22][CH3:21])[CH:24]=3)[CH2:29][CH2:30]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 30872911H-Benzimidazole-2-carboxamide, N-2-pyridinyl-HCID 118091532-[4-(3,4-Dimethoxybenzoyl)-1-piperazinyl]ethyl chloride

Product 1

HCID 14371294N-(2-pyridyl)-1-[2-(4-(3,4-dimethoxybenzoyl)-1-piperazinyl)ethyl]benzimidazole-2-carboxamideYield 52.9%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

In an argon atmosphere, N-(2-pyridyl)benzimidazole-2-carboxamide (1.40 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-(3,4-dimethoxybenzoyl)-1-piperazinyl]ethyl chloride (1.90 g) in DMSO was added dropwise and allowed to react overnight at room temperature under agitation. The reaction solution was poured into an aqueous solution of ammonium chloride and extracted with chloroform. The chloroform layer was dried over Na2SO4 and the solvent was distilled off. Purification of the residue by column chromatography on silica gel gave the title compound (1.60 g) as amorphous solid.

Workup

  1. customto react overnight at room temperature under agitation
  2. extractionextracted with chloroform
  3. dry with materialThe chloroform layer was dried over Na2SO4
  4. distillationthe solvent was distilled off
  5. customPurification of the residue by column chromatography on silica gel

Sources & evidence

ORD record
ord-69740c2500544e618dec4d0230f5d979
Source dataset
uspto-grants-1989_12
Patent number
US04886803

Linked notes

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