Sodium hydride → N-Methyl-N-(4,6-dimethyl-2-pyridyl)-1-[2-(4-(3,4-dimethoxybenzoyl)-1-piperazinyl)ethyl]benzimidazole-2-carboxamide

HRID 476896

Reaction equation

HRID 476896 reaction equation
[CH3:1][N:2]([C:14]1[CH:19]=[C:18]([CH3:20])[CH:17]=[C:16]([CH3:21])[N:15]=1)[C:3]([C:5]1[NH:6][C:7]2[CH:13]=[CH:12][CH:11]=[CH:10][C:8]=2[N:9]=1)=[O:4].[H-].[Na+].[CH3:24][O:25][C:26]1[CH:27]=[C:28]([CH:40]=[CH:41][C:42]=1[O:43][CH3:44])[C:29]([N:31]1[CH2:36][CH2:35][N:34]([CH2:37][CH2:38]Cl)[CH2:33][CH2:32]1)=[O:30].[Cl-].[NH4+]>CS(C)=O>[CH3:1][N:2]([C:14]1[CH:19]=[C:18]([CH3:20])[CH:17]=[C:16]([CH3:21])[N:15]=1)[C:3]([C:5]1[N:6]([CH2:38][CH2:37][N:34]2[CH2:35][CH2:36][N:31]([C:29](=[O:30])[C:28]3[CH:40]=[CH:41][C:42]([O:43][CH3:44])=[C:26]([O:25][CH3:24])[CH:27]=3)[CH2:32][CH2:33]2)[C:7]2[CH:13]=[CH:12][CH:11]=[CH:10][C:8]=2[N:9]=1)=[O:4]

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 118091532-[4-(3,4-Dimethoxybenzoyl)-1-piperazinyl]ethyl chlorideHCID 14371319N-methyl-N-(4,6-dimethyl-2-pyridyl)benzimidazole-2-carboxamide

Product 1

HCID 9809995N-Methyl-N-(4,6-dimethyl-2-pyridyl)-1-[2-(4-(3,4-dimethoxybenzoyl)-1-piperazinyl)ethyl]benzimidazole-2-carboxamideYield 79.2%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

In an argon atmosphere, N-methyl-N-(4,6-dimethyl-2-pyridyl)benzimidazole-2-carboxamide (2.00 g) was dissolved in DMSO (15 ml), and 60% sodium hydride (0.33 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 (2.20 g) in DMSO was added dropwise and allowed to react overnight at room temperature under agitation. The reaction solution was added to 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 gave the title compound (3.10 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

Sources & evidence

ORD record
ord-f6323285af62467588d63c16ce98f4cc
Source dataset
uspto-grants-1989_12
Patent number
US04886803

Linked notes

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