Hydrochloric Acid → Benzyl 4-oxopiperidine-1-carboxylate

HRID 1781995Notes

Reaction equation

HRID 1781995 reaction equation
O.Cl.[NH:3]1[CH2:8][CH2:7][C:6](=[O:9])[CH2:5][CH2:4]1.[CH2:10]([O:17][C:18](Cl)=[O:19])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.Cl>[OH-].[Na+]>[CH2:10]([O:17][C:18]([N:3]1[CH2:8][CH2:7][C:6](=[O:9])[CH2:5][CH2:4]1)=[O:19])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 10387Benzyl chloroformateHCID 2723901Piperonylamine

Product 1

HCID 643496Benzyl 4-oxopiperidine-1-carboxylateYield 100.3%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

A 4-piperidone hydrochloride monohydrate (15.3 g) was dissolved in 2N aqueous solution of sodium hydroxide (100 mL). To the solution was added a benzyloxycarbonyl chloride (20.4 g) at 0° C. The mixture was stirred for 1 hour. The reaction mixture was neutralized with 2N hydrochloric acid, and the aqueous solution was extracted three times with ethyl acetate. The organic layer was washed with a saturated aqueous solution of sodium bicarbonate and a saturated aqueous solution of sodium chloride subsequently, dried over anhydrous magnesium sulfate and concentrated to give the title compound (23.3 g) having the following physical data.

Workup

  1. extractionthe aqueous solution was extracted three times with ethyl acetate
  2. washThe organic layer was washed with a saturated aqueous solution of sodium bicarbonate
  3. dry with materiala saturated aqueous solution of sodium chloride subsequently, dried over anhydrous magnesium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-47698fe631f744f7bb78fc6f4bd9c905
Source dataset
uspto-grants-2009_03
Patent number
US07498323B2

Reaction notes

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