Triethylamine → Ethyl 4-oxo-1-piperidinecarboxylate

HRID 2093086Notes

Reaction equation

HRID 2093086 reaction equation
Cl.N1CCCC[C:3]1=[O:8].CC[N:11]([CH2:14][CH3:15])[CH2:12][CH3:13].Cl[C:17]([O:19][CH2:20][CH3:21])=[O:18]>ClCCl.C(Cl)(Cl)Cl>[O:8]=[C:3]1[CH2:13][CH2:12][N:11]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH2:14][CH2:15]1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 20088740Piperidin-2-one--hydrogen chloride (1/1)

Product 1

HCID 34767Ethyl 4-oxo-1-piperidinecarboxylate

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of a piperidone hydrochloride (1 eq) in dichloromethane was added Et3N (2.1 eq) at 0° C. and the reaction mixture was stirred for 15 min. A solution ethyl chloroformate (1.1 eq) in chloroform was added at 0° C. and reaction was continued at room temperature for 3 h Reaction was quenched with water and extracted with ethyl acetate, organic layer was separated, dried over anhydrous Na2SO4 and concentrated under reduced pressure to afford crude product, which, on purification by column chromatography afforded the desired ethyl 4-oxopiperidine-1-carboxylate.

Workup

  1. customreaction
  2. waitwas continued at room temperature for 3 h
  3. customReaction
  4. customwas quenched with water
  5. extractionextracted with ethyl acetate, organic layer
  6. customwas separated
  7. dry with materialdried over anhydrous Na2SO4
  8. concentrationconcentrated under reduced pressure
  9. customto afford crude product, which
  10. customon purification by column chromatography

Sources & evidence

ORD record
ord-0e613af0ef2144679d6c12fc7a0799a7
Source dataset
uspto-grants-2013_05
Patent number
US08440830B2

Reaction notes

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