Potassium Carbonate → 6-[(Dimethylamino)methyl]-7-hydroxy-1-(2-methoxyethyl)-N,N,2-trimethyl-1H-benzimidazole-5-carboxamide

HRID 1258465Notes

Reaction equation

HRID 1258465 reaction equation
[OH:1][C:2]1[C:7]2[N:8]([CH2:12][CH2:13][O:14][CH3:15])[C:9]([CH3:11])=[N:10][C:6]=2[CH:5]=[C:4]([C:16]([N:18]([CH3:20])[CH3:19])=[O:17])[CH:3]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH3:7][N:8]([CH2:12][C:3]1[C:4]([C:16]([N:18]([CH3:20])[CH3:19])=[O:17])=[CH:5][C:6]2[N:10]=[C:9]([CH3:11])[N:8]([CH2:12][CH2:13][O:14][CH3:15])[C:7]=2[C:2]=1[OH:1])[CH3:9]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 672205657-Hydroxy-1-(2-methoxyethyl)-N,N,2-trimethyl-1H-benzimidazole-5-carboxamide

Product 1

HCID 672203476-[(Dimethylamino)methyl]-7-hydroxy-1-(2-methoxyethyl)-N,N,2-trimethyl-1H-benzimidazole-5-carboxamideYield 142%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 7-hydroxy-1-(2-methoxyethyl)-N,N,2-trimethyl-1H-benzimidazole-5-carboxamide (1.0 g, 3.6 mmol, Step 2) and potassium carbonate (748 mg, 5.4 mmol) in N,N-dimethylformamide (36 mL) at 0° C. was added N,N-dimethylmethyleneiminium iodide (867 mg, 4.7 mmol). After stirring at the same temperature for 4 hours, the reaction mixture was quenched with saturated sodium hydrogencarbonate aqueous solution and extracted with dichloromethane. The combined organic layer was washed with brine, dried over magnesium sulfate, and concentrated in vacuo. The residue was purified by column chromatography on NH-gel eluting with ethyl acetate/methanol (30:1) to afford the title compound (855 mg, 71%) as a white amorphous.

Workup

  1. customthe reaction mixture was quenched with saturated sodium hydrogencarbonate aqueous solution
  2. extractionextracted with dichloromethane
  3. washThe combined organic layer was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by column chromatography on NH-gel
  7. washeluting with ethyl acetate/methanol (30:1)

Sources & evidence

ORD record
ord-b40c95a2048b4cc7bfbb476514732319
Source dataset
uspto-grants-2013_06
Patent number
US08466166B2

Reaction notes

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