Pivaloyl chloride → Ethyl 1-(2,2-dimethyl-1-oxopropyl)-4-oxo-3-piperidinecarboxylate

HRID 1198460Notes

Reaction equation

HRID 1198460 reaction equation
Cl.[C:2]([CH:7]1[C:12](=[O:13])[CH2:11][CH2:10][NH:9][CH2:8]1)([O:4][CH2:5][CH3:6])=[O:3].[CH3:14][C:15]([CH3:20])([CH3:19])[C:16](Cl)=[O:17]>C(=O)([O-])[O-].[Na+].[Na+]>[CH3:14][C:15]([CH3:20])([CH3:19])[C:16]([N:9]1[CH2:10][CH2:11][C:12](=[O:13])[CH:7]([C:2]([O:4][CH2:5][CH3:6])=[O:3])[CH2:8]1)=[O:17]

Participants

4

Reactant 2

HCID 62493Pivaloyl chlorideHCID 1073153-Piperidinecarboxylic acid, 4-oxo-, ethyl ester, hydrochloride (1:1)

Product 1

HCID 19102683Ethyl 1-(2,2-dimethyl-1-oxopropyl)-4-oxo-3-piperidinecarboxylate

Reagents, catalysts & solvents 1

HCID 10340Sodium CarbonateSolvent

Procedure

To a mixture of 2.0 g of 3-carbethoxy-4-piperidone hydrochloride and 20 ml of 1M sodium carbonate is cooled in an ice bath and rapidly treated with 1.3 ml of trimethylacetyl chloride. Stirring is continued in the cold for 1.5 hours. The reaction mixture is filtered and the collected solid washed with water, air dried and then dried at 56° C. for 1.25 hours under high vacuum to afford 1.4 g of the desired product as a colorless solid, m.p. 46°-50° C.

Workup

  1. temperatureis cooled in an ice bath
  2. customcold for 1.5 hours
  3. filtrationThe reaction mixture is filtered
  4. washthe collected solid washed with water, air
  5. customdried
  6. customdried at 56° C. for 1.25 hours under high vacuum

Sources & evidence

ORD record
ord-021f6671d14942febf33909459976230
Source dataset
uspto-grants-1994_01
Patent number
US05281602

Reaction notes

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