Methyl iodide → 1-(1-Benzyl-4-methyl-piperidin-4-yl)-3-methyl-1,3-dihydro-benzoimidazol-2-one

HRID 239119Notes

Reaction equation

HRID 239119 reaction equation
[CH3:1]I.[CH2:3]([N:10]1[CH2:15][CH2:14][C:13]([N:17]2[C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=3[NH:19][C:18]2=[O:26])([CH3:16])[CH2:12][CH2:11]1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[H-].[Na+]>O>[CH2:3]([N:10]1[CH2:15][CH2:14][C:13]([N:17]2[C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=3[N:19]([CH3:1])[C:18]2=[O:26])([CH3:16])[CH2:12][CH2:11]1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 866864921-(1-Benzyl-4-methyl-piperidin-4-yl)-1,3-dihydro-benzoimidazol-2-one

Product 1

HCID 866864931-(1-Benzyl-4-methyl-piperidin-4-yl)-3-methyl-1,3-dihydro-benzoimidazol-2-oneYield 46.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

170 mg methyliodide was added to 320 mg 1-(1-benzyl-4-methyl-piperidin-4-yl)-1,3-dihydro-benzoimidazol-2-one and 50 mg sodium hydride (60% oil dispersion). The reaction was stirred 1 h at RT. The reaction was diluted with water and extracted with ethylacetate. The organic layer was evaporated and the residue was purified by column chromatographie on silica gel (heptane/ethylacetate/triethylamine:1/1/0.01) to give 155 mg of the desired product.

Workup

  1. extractionextracted with ethylacetate
  2. customThe organic layer was evaporated
  3. customthe residue was purified by column chromatographie on silica gel (heptane/ethylacetate/triethylamine:1/1/0.01)

Sources & evidence

ORD record
ord-a44fdd22af84412289c633c6fcdd14d5
Source dataset
uspto-grants-2014_02
Patent number
US08642774B2

Reaction notes

Loading…