Sodium ethoxide → Ethyl 1-Ethyl-2,4-dioxopiperidine-3-carboxylate

HRID 1252279Notes

Reaction equation

HRID 1252279 reaction equation
[Na].[O-]CC.[Na+].[CH2:6]([O:8][C:9]([CH2:11][C:12]([N:14]([CH2:22][CH3:23])[CH2:15][CH2:16][C:17]([O:19]CC)=O)=[O:13])=[O:10])[CH3:7]>C(O)C>[C:9]([CH:11]1[C:17](=[O:19])[CH2:16][CH2:15][N:14]([CH2:22][CH3:23])[C:12]1=[O:13])([O:8][CH2:6][CH3:7])=[O:10]

Participants

5

Reactant 3

HCID 2723922Sodium ethoxideHCID 5360545SodiumHCID 13784117ethyl N-ethoxycarbonylacetyl-3-ethylaminopropionate

Product 1

HCID 13784118Ethyl 1-Ethyl-2,4-dioxopiperidine-3-carboxylateYield 71%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

5.8 g of metallic sodium was added to 300 ml of ethanol and they were reacted to obtain an ethanol solution containing sodium ethoxide. To this solution was added 62.2 g of ethyl N-ethoxycarbonylacetyl-3-ethylaminopropionate, and they were refluxed for 4 hours and allowed to cool. Ethanol was distilled off. Thereto were added ethyl acetate and a dilute aqueous hydrochloric acid solution and the resulting mixture was shaken. The organic layer was separated, water-washed, dried and concentrated to obtain 36.3 g of 3-carboethoxy-1-ethylpiperidine-2,4-dione as an oily matter with an yield of 71%.

Workup

  1. customwere reacted
  2. temperaturewere refluxed for 4 hours
  3. temperatureto cool
  4. distillationEthanol was distilled off
  5. additionThereto were added ethyl acetate
  6. customThe organic layer was separated
  7. washwater-washed
  8. customdried
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-1fd6fe2772494ec993726d59493f8be5
Source dataset
uspto-grants-1988_05
Patent number
US04742165

Reaction notes

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