2,2-Diethoxyethylamine → 2,2-Dimethoxy-n-[(1-methyl-1h-benzimidazol-2-yl)methyl]ethanamine

HRID 643081

Reaction equation

HRID 643081 reaction equation
[CH3:1][N:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[N:4]=[C:3]1[CH:11]=O.[CH2:13]([O:15][CH:16]([O:19][CH2:20]C)[CH2:17][NH2:18])C.[BH3-]C#N.[Na+]>CO.C(O)(=O)C>[CH3:13][O:15][CH:16]([O:19][CH3:20])[CH2:17][NH:18][CH2:11][C:3]1[N:2]([CH3:1])[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[N:4]=1

Participants

6

Reactant 3

HCID 695242,2-DiethoxyethylamineHCID 7620841-methyl-1H-1,3-benzodiazole-2-carbaldehydeHCID 5003444Sodium cyanoborohydride

Product 1

HCID 552185252,2-Dimethoxy-n-[(1-methyl-1h-benzimidazol-2-yl)methyl]ethanamineYield 77.1%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

A solution of 1-methyl-2-formylbenzimidazole (1 g) in methanol (27 mL) and acetic acid (0.54 mL) was treated with aminoacetaldehyde diethylacetal (0.9 g, 1 equivalent) and NaCNBH3 (0.85 g, 2 equivalents) at 25° C., stirred for 1 hour. The mixture was partitioned between water and ethyl acetate. The organic layer was separated, washed sequentially with saturated NaHCO3 and brine, and concentrated. The residue was purified by eluting with 8% methanol/dichloromethane to give 1.2 g (64%) of the title compound.

Workup

  1. customThe mixture was partitioned between water and ethyl acetate
  2. customThe organic layer was separated
  3. washwashed sequentially with saturated NaHCO3 and brine
  4. concentrationconcentrated
  5. customThe residue was purified
  6. washby eluting with 8% methanol/dichloromethane

Sources & evidence

ORD record
ord-ad9d204e608a4e9bbacd289dd9b366e6
Source dataset
uspto-grants-2010_04
Patent number
US07696226B2

Linked notes

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