Methylamine → ((1H-1,3-benzodiazol-2-yl)methyl)(methyl)amine dihydrochloride

HRID 1601066Notes

Reaction equation

HRID 1601066 reaction equation
[CH3:1][NH2:2].[Cl:3][CH2:4][C:5]1[NH:6][C:7]2[CH:13]=[CH:12][CH:11]=[CH:10][C:8]=2[N:9]=1>CCOCC.CCO>[ClH:3].[ClH:3].[CH3:1][NH:2][CH2:4][C:5]1[NH:6][C:7]2[CH:13]=[CH:12][CH:11]=[CH:10][C:8]=2[N:9]=1

Participants

5

Reactant 2

HCID 6329MethylamineHCID 785712-Chloromethylbenzimidazole

Product 1

HCID 13169407((1H-1,3-benzodiazol-2-yl)methyl)(methyl)amine dihydrochlorideYield 26.7%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 3283Diethyl EtherSolvent2×

Procedure

Methylamine (5.0 g, 0.16 mole) was dissolved in a solution of Et2O (100 mL) and EtOH (5 mL) at 0° C., and 2-chloromethylbenzimidazole (13.4 g, 0.08 mole) was added in small portions. The reaction mixture was stirred at RT for 3 h, then was allowed to stand at RT overnight. More Et2O (200 mL) was added, and the reaction was cooled in an ice bath for 3 h before filtering off the precipitate. The filtrate was saturated with HCl and filtered, and the filtrate was concentrated. Silica gel chromatography (step gradient, 10-25% MeOH/CH2Cl2) yielded the title compound (2.5 g, 13%): 1H NMR (250 MHz, 5:1 DMSO-d6 /CDCl3) δ 7.13-7.54 (m, 4H), 4.11 (s, 2H), 2.50 (s, 3H); MS (ES) m/e 162.0 (M+H)+.

Workup

  1. waitto stand at RT overnight
  2. temperaturethe reaction was cooled in an ice bath for 3 h
  3. filtrationbefore filtering off the precipitate
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-30287ae4c1c7437aa9410665e4ce3da8
Source dataset
uspto-grants-1999_11
Patent number
US05977101

Reaction notes

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