Benzimidazole → 1-(1H-benzimidazol-1-ylmethyl)-4-propyl-pyrrolidin-2-one

HRID 2358243Notes

Reaction equation

HRID 2358243 reaction equation
O[CH2:2][N:3]1[CH2:7][CH:6]([CH2:8][CH2:9][CH3:10])[CH2:5][C:4]1=[O:11].[N:12]1[C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=2[NH:14][CH:13]=1>C(O)(=O)C>[N:12]1([CH2:2][N:3]2[CH2:7][CH:6]([CH2:8][CH2:9][CH3:10])[CH2:5][C:4]2=[O:11])[C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=2[N:14]=[CH:13]1

Participants

4

Reactant 2

HCID 5798BenzimidazoleHCID 113326021-(Hydroxymethyl)-4-propylpyrrolidin-2-one

Product 1

HCID 114368011-(1H-benzimidazol-1-ylmethyl)-4-propyl-pyrrolidin-2-one

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

In a 50 ml three necked flask fitted with a magnetic stirrer, under inert atmosphere, a solution of 1-(hydroxymethyl)-4-propyl-pyrrolidin-2-one a24 (2.5 mmol, 400 mg) and benzimidazole (1 eq, 2.5 mmol, 300 mg) in acetic acid (20 ml) was heated at reflux overnight. After cooling, acetic acid was removed under vacuum, and the crude product was purified by preparative chromatography on silicagel to give 1-(1H-benzimidazol-1-ylmethyl)-4-propyl-pyrrolidin-2-one 91 after recrystallization in diisopropylether (16%).

Workup

  1. temperatureat reflux overnight
  2. temperatureAfter cooling
  3. customacetic acid was removed under vacuum
  4. customthe crude product was purified by preparative chromatography on silicagel

Sources & evidence

ORD record
ord-44548a202c2945bb8faaabd9b7e956e4
Source dataset
uspto-grants-2010_07
Patent number
US07763644B2

Reaction notes

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