HCID 67043500, compound → 6-phenylpiperidin-2-one

HRID 539626Notes

Reaction equation

HRID 539626 reaction equation
CO[C:3](=O)[CH2:4][CH2:5][CH:6]([NH:13][C:14]([O:16]CC1C=CC=CC=1)=O)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1>CCO.[Pd]>[C:7]1([CH:6]2[NH:13][C:14](=[O:16])[CH2:3][CH2:4][CH2:5]2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

4

Reactant 1

HCID 67043500HCID 67043500, compound

Product 1

HCID 6002256-phenylpiperidin-2-oneYield 81%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Conditions

Temperature
65 °C

Procedure

4-Benzyloxycarbonylamino-4-phenyl-butyric acid methyl ester was dissolved in EtOH (30 mL), and 10% palladium on activated carbon (1.1 g) was added. The mixture was stirred under hydrogen atmosphere at 45 psi (3.1 bar) for 22 hours at room temperature and 4 hours at 65° C. The mixture was filtered and the filtrated was concentrated under reduced pressure. The residue was recrystallized from a mixture of methanol, diethyl ether and hexanes to give 1.85 g (81%) of 6-phenyl-piperidin-2-one as colorless crystals.

Workup

  1. filtrationThe mixture was filtered
  2. concentrationthe filtrated was concentrated under reduced pressure
  3. customThe residue was recrystallized from a mixture of methanol, diethyl ether and hexanes

Sources & evidence

ORD record
ord-ea687a8a672046f48af8589e5595dd3b
Source dataset
uspto-grants-2014_10
Patent number
US08871760B2

Reaction notes

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