1-Methylpiperazine → 2-(4-Methyl-1-piperazinyl)-1H-benzimidazole

HRID 1388159Notes

Reaction equation

HRID 1388159 reaction equation
Cl[C:2]1[NH:3][C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=1.[CH3:11][N:12]1[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1>[OH-].[Na+]>[CH3:11][N:12]1[CH2:17][CH2:16][N:15]([C:2]2[NH:3][C:4]3[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=3[N:6]=2)[CH2:14][CH2:13]1

Participants

4

Reactant 2

HCID 531671-MethylpiperazineHCID 785722-Chlorobenzimidazole

Product 1

HCID 27731802-(4-Methyl-1-piperazinyl)-1H-benzimidazoleYield 49.5%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Conditions

Temperature
125 °C

Procedure

A mixture of 2-chlorobenzimidazole (10.00 g) and N-mehylpiperazine (20.00 g) is stirred at 125° C. for 5 hours. A 10% aqueous sodium hydroxide (100 ml) is added to the reaction mixture, and the precipitated crystals are separated by filtration. The filtrate is extracted with chloroform, and the chloroform extract is evaporated to dryness to give the same crystals. The crystals are combined and recrystallized from water-methanol to give 2-(4-methyl-1-piperazinyl)benzimidazole (7.02 g) as colorless needles, m.p. 225°-226° C.

Workup

  1. customthe precipitated crystals are separated by filtration
  2. extractionThe filtrate is extracted with chloroform
  3. extractionthe chloroform extract
  4. customis evaporated to dryness
  5. customto give the same crystals
  6. customrecrystallized from water-methanol

Sources & evidence

ORD record
ord-a71148776e564f51b0ed2c95a2b57214
Source dataset
uspto-grants-1984_02
Patent number
US04430343

Reaction notes

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