2-Chlorobenzimidazole → N-Methyl-N-(1-methyl-3-pyrrolidinyl)-1H-benzimidazol-2-amine

HRID 1031172Notes

Reaction equation

HRID 1031172 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][NH:12][CH:13]1[CH2:17][CH2:16][N:15]([CH3:18])[CH2:14]1>[OH-].[Na+]>[CH3:11][N:12]([CH:13]1[CH2:17][CH2:16][N:15]([CH3:18])[CH2:14]1)[C:2]1[NH:3][C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=1

Participants

4

Reactant 2

HCID 785722-ChlorobenzimidazoleHCID 2758520N,1-dimethylpyrrolidin-3-amine

Product 1

HCID 19819773N-Methyl-N-(1-methyl-3-pyrrolidinyl)-1H-benzimidazol-2-amineYield 40%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 2-chlorobenzimidazole (25 g, 0.165 mol) and 3-methylamino-1-methylpyrrolidine (72 g, 0.63 mol) was heated at 120° C. with an oil bath for 18 hr. After cooling, 500 ml of 2.5N NaOH solution was added and the mixture extracted twice with 100 ml portions of methylene chloride. The methylene chloride extracts were combined and washed successively with 2×100 ml portions of 2.5N NaOH solution and 3×100 ml portions of water. The methylene chloride solution was dried (Na2SO4) and concentrated to obtain 15 g of product (40% yield).

Workup

  1. temperatureAfter cooling
  2. extractionthe mixture extracted twice with 100 ml portions of methylene chloride
  3. washwashed successively with 2×100 ml portions of 2.5N NaOH solution and 3×100 ml portions of water
  4. dry with materialThe methylene chloride solution was dried (Na2SO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-0ea9a0144697450ab80f4489e9bc5bd8
Source dataset
uspto-grants-1992_04
Patent number
US05109013

Reaction notes

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