Sodium hydride → 1-Methyl-3-phenylpiperidin-4-one

HRID 851011Notes

Reaction equation

HRID 851011 reaction equation
C(OC([CH2:6][CH2:7][N:8]([CH3:22])[CH2:9][CH:10]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:11]([O:13]CC)=O)=O)C.[H-].[Na+].[H][H]>C1(C)C=CC=CC=1>[CH3:22][N:8]1[CH2:7][CH2:6][C:11](=[O:13])[CH:10]([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH2:9]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 12788375Ethyl 3-((3-ethoxy-3-oxopropyl)(methyl)amino)-2-phenylpropanoateHCID 178418361HCID 178418361, compound

Product 1

HCID 127885251-Methyl-3-phenylpiperidin-4-one

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

208.78 g of ethyl N-(2-ethoxycarbonylethyl)-3-methylamino-2-phenylpropionate, 10 ml of absolute alcohol and 500 ml of toluene are added to a suspension of 65.28 g of sodium hydride and 3.0 l of toluene. When hydrogen evolution slows (about 0.5 hour), the mixture is heated to reflux for 30 minutes. The reaction mixture is cooled and then extracted with 6 N hydrochloric acid. The resultant acid extracts are washed with 500 ml of hexane and heated to reflux under nitrogen for two hours. The mixture is then cooled, basified with 50 weight percent aqueous NaOH solution (1.6 l) and then extracted with ether. The ether extracts are dried over Na2SO4 and then filtered. The filtrate is concentrated in vacuo to yield an oil product of 1-methyl-3-phenyl-4-piperidone.

Workup

  1. custom(about 0.5 hour)
  2. temperaturethe mixture is heated
  3. temperatureto reflux for 30 minutes
  4. temperatureThe reaction mixture is cooled
  5. extractionextracted with 6 N hydrochloric acid
  6. washThe resultant acid extracts are washed with 500 ml of hexane
  7. temperatureheated
  8. temperatureto reflux under nitrogen for two hours
  9. temperatureThe mixture is then cooled
  10. extractionextracted with ether
  11. dry with materialThe ether extracts are dried over Na2SO4
  12. filtrationfiltered
  13. concentrationThe filtrate is concentrated in vacuo

Sources & evidence

ORD record
ord-f9979f7cf29a4cba9b8fdddbd9e235d0
Source dataset
uspto-grants-1983_05
Patent number
US04382141

Reaction notes

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