Triethylamine → Ethyl 4-oxo-1-piperidinecarboxylate

HRID 1523727Notes

Reaction equation

HRID 1523727 reaction equation
Cl.[NH:2]1[CH2:7][CH2:6][C:5](=[O:8])[CH2:4][CH2:3]1.C(N(CC)CC)C.[CH2:16]([O:18][C:19](Cl)=[O:20])[CH3:17]>C(Cl)Cl.O>[O:8]=[C:5]1[CH2:6][CH2:7][N:2]([C:19]([O:18][CH2:16][CH3:17])=[O:20])[CH2:3][CH2:4]1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 30848514-Piperidone hydrochloride

Product 1

HCID 34767Ethyl 4-oxo-1-piperidinecarboxylateYield 98%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To the stirred solution of piperidin-4-one hydrochloride (2.0 g, 14.7 mmol) in DCM (60 mL) cooled at 0° C., was added triethylamine (5.15 mL, 36.75 mmol) and ethylchloroformate (1.59 mL, 16.6 mml). The reaction mixture was stirred at room temperature for 2 hours before being diluted with water. The two layers were separated, the organic layer was dried over anhydrous sodium sulfate and the volatiles were removed under reduced pressure to obtain ethyl 4-oxo-piperidine-1-carboxylate (3.14 grams).

Workup

  1. customThe two layers were separated
  2. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  3. customthe volatiles were removed under reduced pressure

Sources & evidence

ORD record
ord-3f29d267bb1644e8b6c7dfb977c708b9
Source dataset
uspto-grants-2015_07
Patent number
US09079894B2

Reaction notes

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