Methyl iodide → HCID 11318457, compound

HRID 1820318Notes

Reaction equation

HRID 1820318 reaction equation
[H-].[Na+].O[CH2:4][CH:5]([CH2:37][OH:38])[CH2:6][CH2:7][C:8]1([CH2:14][CH2:15][N:16]2[CH2:21][CH2:20][CH:19]([N:22]([C:30]3[CH:35]=[CH:34][C:33]([CH3:36])=[CH:32][N:31]=3)[C:23]([C:25]3[O:26][CH:27]=[CH:28][CH:29]=3)=[O:24])[CH2:18][CH2:17]2)[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1.[CH3:39]I.[C:41](=[O:44])([O-])O.[Na+]>CN(C)C=O>[CH3:39][O:38][CH2:37][CH:5]([CH2:4][O:44][CH3:41])[CH2:6][CH2:7][C:8]1([CH2:14][CH2:15][N:16]2[CH2:21][CH2:20][CH:19]([N:22]([C:30]3[CH:35]=[CH:34][C:33]([CH3:36])=[CH:32][N:31]=3)[C:23]([C:25]3[O:26][CH:27]=[CH:28][CH:29]=3)=[O:24])[CH2:18][CH2:17]2)[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13]1

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 516892Sodium BicarbonateHCID 23109904HCID 23109904, compound

Product 1

HCID 11318457HCID 11318457, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

After adding sodium hydride (60% dispersion in mineral oil) (179 mg, 4.47 mmol) to a solution of N-[1-[2-[1-(4-hydroxy-3-hydroxymethylbutyl)cyclohexyl]ethyl]piperidin-4-yl]-N-(5-methylpyridin-2-yl)-2-furancarboxamide (1.00 g, 2.01 mmol) in N,N-dimethylformamide (3 mL) while cooling on ice, the mixture was stirred for 40 minutes. Next, methyl iodide (0.15 mL, 2.41 mmol) was added, stirring was continued for 1 hour, and saturated aqueous sodium hydrogencarbonate (10 mL) was added. Extraction was performed with ethyl acetate, and the extract was washed with saturated aqueous sodium chloride (10 mL) and then dried over anhydrous magnesium sulfate. The residue obtained after filtering and concentration under reduced pressure was purified by silica gel column chromatography (150 g NH silica Chromatorex DM2035, hexane:ethyl acetate=1:1-chloroform:methanol=8:2) to obtain the title compound (100 mg) and a furancarboxylic acid ester of N-[1-[2-[1-(4-methoxy-3-hydroxymethylbutyl)cyclohexyl]ethyl]piperidin-4-yl]-N-(5-methylpyridin-2-yl)-2-furancarboxamide (91 mg).

Workup

  1. temperaturewhile cooling on ice
  2. stirringstirring
  3. waitwas continued for 1 hour
  4. extractionExtraction
  5. washthe extract was washed with saturated aqueous sodium chloride (10 mL)
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customThe residue obtained
  8. filtrationafter filtering
  9. concentrationconcentration under reduced pressure
  10. customwas purified by silica gel column chromatography (150 g NH silica Chromatorex DM2035, hexane:ethyl acetate=1:1-chloroform:methanol=8:2)

Sources & evidence

ORD record
ord-e45ff8390401463caf0537086ff37298
Source dataset
uspto-grants-2009_10
Patent number
US07601843B2

Reaction notes

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