Dimethylformamide → HCID 19807300, compound

HRID 1681175Notes

Reaction equation

HRID 1681175 reaction equation
[CH3:1]N(C)C=O.[ClH:6].[C:7]1(/[CH:13]=[CH:14]/[C:15]([NH:17][CH2:18][CH2:19][CH:20]2[CH2:25][CH2:24][N:23]([CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[CH2:22][CH2:21]2)=[O:16])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[H-].[Na+].CI>O>[ClH:6].[C:7]1(/[CH:13]=[CH:14]/[C:15]([N:17]([CH3:1])[CH2:18][CH2:19][CH:20]2[CH2:25][CH2:24][N:23]([CH2:26][C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=3)[CH2:22][CH2:21]2)=[O:16])[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 14553494HCID 14553494, compound

Product 1

HCID 19807300HCID 19807300, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

To a dimethylformamide solution (5 ml) of (E)-3-phenyl-N-[2-(1-benzylpiperidin-4-yl)ethyl]-2-propenamide.hydrochloride (0.6 g) obtained in Example 1 was gradually added sodium hydride (80 mg) at room temperature and the mixture was stirred at 60° C. for 30 minutes. The reaction mixture was cooled on an ice-bath and there was added methyl iodide (0.21 g), followed by stirring at room temperature for one hour. To the resultant mixture was added water and the mixture was subjected to extraction with dichloromethane. The dichloromethane solution was washed with water and dried over anhydrous sodium sulfate, then the solvent was distilled off. The oily residue was subjected to a silica gel column chromatography [developing solvent : ethyl acetate - methanol=10 : 1(V/V)]. Then the solvent of the solution containing the object compound was distilled off. To the residue was added an ethanolic solution (0.5 ml) of 3N hydrogen chloride, followed by distilling off the solvent to obtain an amorphous powder (0.2 g).

Workup

  1. customat room temperature
  2. temperatureThe reaction mixture was cooled on an ice-bath
  3. stirringby stirring at room temperature for one hour
  4. extractionthe mixture was subjected to extraction with dichloromethane
  5. washThe dichloromethane solution was washed with water
  6. dry with materialdried over anhydrous sodium sulfate
  7. distillationthe solvent was distilled off
  8. additionThen the solvent of the solution containing the object compound
  9. distillationwas distilled off
  10. additionTo the residue was added an ethanolic solution (0.5 ml) of 3N hydrogen chloride
  11. distillationby distilling off the solvent

Sources & evidence

ORD record
ord-1beb42051fad41499b89198ad130e14b
Source dataset
uspto-grants-1992_12
Patent number
US05169856

Reaction notes

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