Benzyl chloroformate → Benzyl 4-oxopiperidine-1-carboxylate

HRID 1419842Notes

Reaction equation

HRID 1419842 reaction equation
Cl.[NH:2]1[CH2:7][CH2:6][C:5](=[O:8])[CH2:4][CH2:3]1.[OH-].[Na+].Cl[C:12]([O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:13]>C1COCC1.O>[CH2:15]([O:14][C:12]([N:2]1[CH2:7][CH2:6][C:5](=[O:8])[CH2:4][CH2:3]1)=[O:13])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

6

Reactant 3

HCID 10387Benzyl chloroformateHCID 14798Sodium HydroxideHCID 30848514-Piperidone hydrochloride

Product 1

HCID 643496Benzyl 4-oxopiperidine-1-carboxylateYield 99.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-piperidone hydrochloride (79.0 g) in THF and water (4: 1,75 ml), was added 4N NaOH (105 ml) solution followed by benzyl chloroformate (66 ml) at 0° C. The resulting mixture was stirred at the same temperature for 1 h. At the end of this time, the mixture was extracted with ethyl acetate and dried over anhydrous sodium sulphate. The solvent was removed by distillation under reduced pressure to give 135 g (99.5%) of the title compound as a dark thick liquid.

Workup

  1. extractionAt the end of this time, the mixture was extracted with ethyl acetate
  2. dry with materialdried over anhydrous sodium sulphate
  3. customThe solvent was removed by distillation under reduced pressure

Sources & evidence

ORD record
ord-bed0c54cf57c4ed2a1d9890130f30cda
Source dataset
uspto-grants-1999_03
Patent number
US05889025

Reaction notes

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