Water → 2-(1-Methylpiperidin-4-ylidene)acetonitrile

HRID 219759Notes

Reaction equation

HRID 219759 reaction equation
C([O-])([O-])=O.[K+].[K+].[C:7]([CH2:9]P(=O)(OCC)OCC)#[N:8].[CH3:18][N:19]1[CH2:24][CH2:23][C:22](=O)[CH2:21][CH2:20]1.O>C1COCC1>[CH3:18][N:19]1[CH2:24][CH2:23][C:22](=[CH:9][C:7]#[N:8])[CH2:21][CH2:20]1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 740491-Methyl-4-piperidoneHCID 75676Diethyl (cyanomethyl)phosphonate

Product 1

HCID 218250202-(1-Methylpiperidin-4-ylidene)acetonitrile

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

9.36 g of K2CO3 and 8.89 ml of diethyl (cyanomethyl)phosphonate are placed in 12 ml of THF in a round-bottomed flask equipped with a magnetic stirrer, and under a stream of nitrogen, and the mixture is left to react for 15 minutes at room temperature and then refluxed for 20 minutes. The resulting mixture is allowed to cool and 6.5 ml of 1-methyl-4-piperidone are added dropwise. This mixture is refluxed for 16 hours. The reaction mixture is then poured into water and extracted with ethyl acetate. The organic phase is dried over Na2SO4, filtered and evaporated under vacuum. 6.8 g of oil are obtained.

Workup

  1. customequipped with a magnetic stirrer
  2. waitunder a stream of nitrogen, and the mixture is left
  3. customto react for 15 minutes at room temperature
  4. temperaturerefluxed for 20 minutes
  5. temperatureto cool
  6. temperatureThis mixture is refluxed for 16 hours
  7. extractionextracted with ethyl acetate
  8. dry with materialThe organic phase is dried over Na2SO4
  9. filtrationfiltered
  10. customevaporated under vacuum

Sources & evidence

ORD record
ord-85c01a36266d4b579c83c44afc59a619
Source dataset
uspto-grants-2012_06
Patent number
US08202871B2

Reaction notes

Loading…