Propanal → 1-Methyl-7-(propylamino)-1,3-dihydro-2H-benzimidazol-2-one

HRID 2235535Notes

Reaction equation

HRID 2235535 reaction equation
[NH2:1][C:2]1[C:7]2[N:8]([CH3:12])[C:9](=[O:11])[NH:10][C:6]=2[CH:5]=[CH:4][CH:3]=1.[CH:13](=O)[CH2:14][CH3:15].C([BH3-])#N.[Na+]>CO>[CH3:12][N:8]1[C:7]2[C:2]([NH:1][CH2:13][CH2:14][CH3:15])=[CH:3][CH:4]=[CH:5][C:6]=2[NH:10][C:9]1=[O:11]

Participants

5

Reactant 3

HCID 527PropanalHCID 5003444Sodium cyanoborohydrideHCID 596354197-Amino-1-methyl-1,3-dihydro-2H-benzo[d]imidazol-2-one

Product 1

HCID 685813791-Methyl-7-(propylamino)-1,3-dihydro-2H-benzimidazol-2-oneYield 63.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To 0.87 g (5.3 mmol) of 7-amino-1-methyl-1,3-dihydro-2H-benzoimidazol-2-one in 50 mL of methanol was added 1.94 mL (26.7 mmol) of propionaldehyde and 1.0 g (16 mmol) of sodium cyanoborohydride. The mixture was stirred at room temperature for 5 h and concentrated in vacuo. The crude solid was partitioned between water and ethyl acetate, the biphasic mixture was filtered to remove particulates and the layers were separated. The organic layer was washed with brine, dried over sodium sulfate, filtered, concentrated and purified by flash chromatography eluting with a 50% ethyl acetate/hexanes mixture to give 0.69 g (63%) of the title compound as a cream colored powder.

Workup

  1. concentrationconcentrated in vacuo
  2. customThe crude solid was partitioned between water and ethyl acetate
  3. filtrationthe biphasic mixture was filtered
  4. customto remove particulates
  5. customthe layers were separated
  6. washThe organic layer was washed with brine
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. custompurified by flash chromatography
  11. washeluting with a 50% ethyl acetate/hexanes mixture

Sources & evidence

ORD record
ord-70641fa3229a40f890cf44dccd53b230
Source dataset
uspto-grants-2010_05
Patent number
US07714009B2

Reaction notes

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