Sodium Hydroxide → 1,3-Dibenzylpiperidin-4-one

HRID 2244130Notes

Reaction equation

HRID 2244130 reaction equation
COC([C:5]1([CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:10](=[O:11])[CH2:9][CH2:8][N:7]([CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:6]1)=O.[OH-].[Na+]>Cl.CO>[CH2:12]([N:7]1[CH2:8][CH2:9][C:10](=[O:11])[CH:5]([CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:6]1)[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 542328573-Carbomethoxy-1,3-dibenzyl-4-piperidone

Product 1

HCID 230036591,3-Dibenzylpiperidin-4-one

Reagents, catalysts & solvents 1

HCID 21893726Hydrochloride methanolSolvent

Procedure

1,3-Dibenzyl-4-oxo-piperidine-3-carboxylic acid methyl ester, (2, Y═H, Z=benzyl) (17.52 g, 51.92 mmol) was suspended in 150 mL of 6N HCl:MeOH (5:1) and the mixture was heated to reflux temperature with stirring for 48 h. After cooling the mixture was basified to pH 10 with 6N NaOH and extracted with 3×200 mL dichloromethane. The combined organics were dried (MgSO4) and concentrated to give 11.60 g of the title compound as a colorless oil, 80%. LC-MS: RT=0.38 min. (M+H)+ 280.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux temperature
  3. temperatureAfter cooling the mixture
  4. extractionextracted with 3×200 mL dichloromethane
  5. dry with materialThe combined organics were dried (MgSO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-c64a19f4f5b341b2a32fcbe2f48f298c
Source dataset
uspto-grants-2010_03
Patent number
US07678813B2

Reaction notes

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