Chloroform → Ethyl 3-oxopiperidine-1-carboxylate

HRID 1415563Notes

Reaction equation

HRID 1415563 reaction equation
C(O[C:4]1([O:10]CC)[CH2:9][CH2:8][CH2:7][NH:6][CH2:5]1)C.C(Cl)(Cl)Cl.Cl[C:18]([O:20][CH2:21][CH3:22])=[O:19]>C(N(CC)CC)C>[C:18]([N:6]1[CH2:7][CH2:8][CH2:9][C:4](=[O:10])[CH2:5]1)([O:20][CH2:21][CH3:22])=[O:19]

Participants

5

Reactant 3

HCID 6212ChloroformHCID 10928Ethyl chloroformateHCID 21482822HCID 21482822, compound

Product 1

HCID 12316089Ethyl 3-oxopiperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Conditions

Temperature
25 °C

Procedure

A solution of 8.7 g. of 3,3-diethoxypiperidine in 100 ml. of dry chloroform is treated at 0° C. with 5 g. of triethylamine followed by 5.4 g. of ethyl chloroformate. After stirring at 25° C. for two hours, the solvent is removed in vacuo. The residue is extracted with ether and the extract concentrated in vacuo. This residue is treated with dilute hydrochloric acid for two hours. The solution is then saturated with sodium chloride and extracted with chloroform. The chloroform extract is washed with 5% aqueous sodium bicarbonate solution, dried and concentrated in vacuo to give 1-carbethoxy-3-piperidone.

Workup

  1. customthe solvent is removed in vacuo
  2. extractionThe residue is extracted with ether
  3. concentrationthe extract concentrated in vacuo
  4. additionThis residue is treated with dilute hydrochloric acid for two hours
  5. extractionsaturated with sodium chloride and extracted with chloroform
  6. extractionThe chloroform extract
  7. washis washed with 5% aqueous sodium bicarbonate solution
  8. customdried
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b17779a56b1c4e65bd9c5299daa7a9a2
Source dataset
uspto-grants-1977_01
Patent number
US04005208

Reaction notes

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