Methyl iodide → HCID 69239194, compound

HRID 1295773Notes

Reaction equation

HRID 1295773 reaction equation
[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]([N:13]2[CH2:18][CH2:17][CH:16]([N:19]3[C:23]4[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=4[NH:21][C:20]3=[S:28])[CH2:15][CH2:14]2)=[O:12])=[CH:7][CH:6]=1)[CH2:2][CH2:3][CH3:4].CI.[C:31](=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH2:1]([C:5]1[CH:6]=[CH:7][C:8]([C:11]([N:13]2[CH2:18][CH2:17][CH:16]([N:19]3[C:23]4[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=4[N:21]=[C:20]3[S:28][CH3:31])[CH2:15][CH2:14]2)=[O:12])=[CH:9][CH:10]=1)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 86589517HCID 86589517, compound

Product 1

HCID 69239194HCID 69239194, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of (4-butyl-phenyl)-[4-(2-thioxo-2,3-dihydro-benzoimidazol-1-yl)-piperidin-1-yl]-methanone (0.167 g, 0.424 mmol) in acetonitrile (5 mL) was treated with methyl iodide (0.120 g, 0.848 mmol) and potassium carbonate (0.117 g, 0.848 mmol). The reaction mixture was stirred 18 h then filtered and concentrated under reduced pressure. The crude product was purified by column chromatography on silica gel using ethyl acetate as the eluent to give (4-butyl-phenyl)-[4-(2-methylsulfanyl-benzoimidazol-1-yl)-piperidin-1-yl]-methanone (0.164 g; 95%).

Workup

  1. filtrationthen filtered
  2. concentrationconcentrated under reduced pressure
  3. customThe crude product was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-dfcd99def99b4a9aacb17355d7086cff
Source dataset
uspto-grants-2007_07
Patent number
US07244744B2

Reaction notes

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