Benzyl 2-(4-fluorophenyl)-4-oxopiperidine-1-carboxylate → 2-(4-Fluorophenyl)-4-piperidinone

HRID 473806Notes

Reaction equation

HRID 473806 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:13][C:12](=[O:14])[CH2:11][CH2:10][N:9]2C(OCC2C=CC=CC=2)=O)=[CH:4][CH:3]=1>C(OCC)(=O)C.O1CCCC1.[Pd]>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:13][C:12](=[O:14])[CH2:11][CH2:10][NH:9]2)=[CH:4][CH:3]=1

Participants

5

Reactant 1

HCID 21927691Benzyl 2-(4-fluorophenyl)-4-oxopiperidine-1-carboxylate

Product 1

HCID 219276782-(4-Fluorophenyl)-4-piperidinoneYield 99.9%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of benzyl 2-(4-fluorophenyl)-4-oxopiperidine-1-carboxylate (4.75 g, 14.50 mmol) in a mixture of ethyl acetate and tetrahydrofuran (1:1, 100 mL) was hydrogenated in the presence of 10% Pd/C at atmospheric pressure over 12 h. The catalyst was filtered off and the filtrate was concentrated. The residue was dissolved in ethyl acetate (250 mL) and washed twice with saturated aqueous bicarbonate (100 mL), brine, then dried over anhydrous sodium sulfate, filtered and concentrated. The residue was dried to give 2-(4-fluorophenyl)piperidin-4-one (2.8 g, quantitative). MS (EI) for C11H12FNO: 194 (MH+).

Workup

  1. filtrationThe catalyst was filtered off
  2. concentrationthe filtrate was concentrated
  3. dissolutionThe residue was dissolved in ethyl acetate (250 mL)
  4. washwashed twice with saturated aqueous bicarbonate (100 mL), brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was dried

Sources & evidence

ORD record
ord-d41c830be4fe4faca5b5a8561da0d1f1
Source dataset
uspto-grants-2014_01
Patent number
US08637499B2

Reaction notes

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