Water → (1H-Benzoimidazol-2-ylmethyl)-methyl-amine

HRID 1030260Notes

Reaction equation

HRID 1030260 reaction equation
Cl[CH2:2][C:3]1[NH:4][C:5]2[CH:11]=[CH:10][CH:9]=[CH:8][C:6]=2[N:7]=1.O.[CH3:13][NH2:14]>>[CH3:13][NH:14][CH2:2][C:3]1[NH:4][C:5]2[CH:11]=[CH:10][CH:9]=[CH:8][C:6]=2[N:7]=1

Participants

4

Reactant 3

HCID 962WaterHCID 6329MethylamineHCID 785712-Chloromethylbenzimidazole

Product 1

HCID 3159692(1H-Benzoimidazol-2-ylmethyl)-methyl-amineYield 22%

Procedure

2-Chloromethylbenzimidazole (3.00 g, 18.01 mmol) was dissolved in aqueous methylamine (50 mL, 40 wt % in H2O) at 10° C. under N2. After 30 minutes, the reaction mixture was warmed to room temperature and stirred for 4 hours. Water was added and the mixture extracted with methylene chloride. The organic phase was dried (MgSO4) and concentrated to afford crude product which was purified by HPLC (gradient methanol/methylene chloride) to afford 0.650 g (22%) of pure product as a tan solid.

Workup

  1. extractionthe mixture extracted with methylene chloride
  2. dry with materialThe organic phase was dried (MgSO4)
  3. concentrationconcentrated
  4. customto afford crude product which
  5. customwas purified by HPLC (gradient methanol/methylene chloride)

Sources & evidence

ORD record
ord-d67342f158d546cb8ea030b072a6cc6b
Source dataset
uspto-grants-1992_04
Patent number
US05104892

Reaction notes

Loading…