Ethyl chloroformate → Ethyl 3-methyl-4-oxopiperidine-1-carboxylate

HRID 466540

Reaction equation

HRID 466540 reaction equation
[CH3:1][CH:2]1[C:7](=[O:8])[CH2:6][CH2:5][N:4](CC2C=CC=CC=2)[CH2:3]1.[C:16](Cl)(=[O:20])[O:17][CH2:18][CH3:19]>CC1C=CC=CC=1>[CH3:1][CH:2]1[C:7](=[O:8])[CH2:6][CH2:5][N:4]([C:16]([O:17][CH2:18][CH3:19])=[O:20])[CH2:3]1

Participants

4

Reactant 2

HCID 10928Ethyl chloroformateHCID 5609651-Benzyl-3-methyl-4-piperidone

Product 1

HCID 15075657Ethyl 3-methyl-4-oxopiperidine-1-carboxylateYield 83%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a stirred solution of 152 parts of 3-methyl-1-(phenylmethyl)-4-piperidinone in 900 parts of methylbenzene were added dropwise 218 parts of ethyl carbonochloridate at room temperature. Upon completion, stirring was continued overnight at reflux. After cooling, the reaction mixture was washed with water and hydrochloric acid, dried, filtered and evaporated. The residue was distilled, yielding 120.5 parts (83%) of ethyl 3-methyl-4-oxo-1-piperidinecarboxylate; bp. 98°-105° C. at 1 mm pressure (intermediate 26).

Workup

  1. temperatureat reflux
  2. temperatureAfter cooling
  3. washthe reaction mixture was washed with water and hydrochloric acid
  4. customdried
  5. filtrationfiltered
  6. customevaporated
  7. distillationThe residue was distilled

Sources & evidence

ORD record
ord-13d868faa37847a28507459d1e747ed7
Source dataset
uspto-grants-1992_10
Patent number
US05157035

Linked notes

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