Ethyl Acetate → Benzyl 4-oxopiperidine-1-carboxylate

HRID 1458784Notes

Reaction equation

HRID 1458784 reaction equation
O.Cl.[NH:3]1[CH2:8][CH2:7][C:6](=[O:9])[CH2:5][CH2:4]1.C(=O)(O)[O-].[K+].C(OCC)(=O)C.Cl[C:22]([O:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[O:23]>O>[CH2:25]([O:24][C:22]([N:3]1[CH2:8][CH2:7][C:6](=[O:9])[CH2:5][CH2:4]1)=[O:23])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 10387Benzyl chloroformateHCID 516893Potassium BicarbonateHCID 2723901Piperonylamine

Product 1

HCID 643496Benzyl 4-oxopiperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

4-Piperidone hydrochloride hydrate (50.0 g, 325 mmol) and potassium bicarbonate (181.9 g, 1.82 mol) were combined in a two phase mixture of ethyl acetate (750 mL) and water (75 mL). Benzyl chloroformate (49 mL, 343 mmol) was added dropwise to the stirred mixture over 10 minutes. The mixture was stirred 2.5 hours, then it was diluted with water (700 mL) and the phases were separated. The aqueous layer was extracted with ethyl acetate and the combined organic phase was washed with water and brine. The organic phase was dried over magnesium sulfate and concentrated to a light yellow oil (76.75 g, 100%). The material was found to be analytically pure and suitable for further transformation without further workup. Analysis calculated for C13H15NO3 : C, 66.94; H, 6.48; N, 6.00. Found: C, 66.67; H, 6.48; N, 5.90.

Workup

  1. customthe phases were separated
  2. extractionThe aqueous layer was extracted with ethyl acetate
  3. washthe combined organic phase was washed with water and brine
  4. dry with materialThe organic phase was dried over magnesium sulfate
  5. concentrationconcentrated to a light yellow oil (76.75 g, 100%)

Sources & evidence

ORD record
ord-97623fb439c14ca184b40916842d1055
Source dataset
uspto-grants-1998_12
Patent number
US05852040

Reaction notes

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