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

HRID 569988Notes

Reaction equation

HRID 569988 reaction equation
[O-]CC.[Na+].[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

To an ethanol solution of sodium ethoxide which had been synthesized by adding 5.8 g of metallic sodium to 300 ml of ethanol, 62.2 g of ethyl N-ethoxycarbonylacetyl-3-ethylaminopropionate (Referential Example 34) was added. The resultant mixture was refluxed for 4 hours. After allowing the reaction mixture to cool down, ethanol was distilled off. Ethyl acetate and a dilute aqueous solution of hydrogen chloride were added. The resulting mixture was shaken. After washing the organic layer with water, it was dried and concentrated to obtain 36.3 g of 3-carboethoxy-1-ethylpiperidine-2,4-dione as an oily substance (yield: 71%).

Workup

  1. additionwas added
  2. temperatureto cool down
  3. distillationethanol was distilled off
  4. additionEthyl acetate and a dilute aqueous solution of hydrogen chloride were added
  5. washAfter washing the organic layer with water, it
  6. customwas dried
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-17bf31bd160649fcb8448678764e0a58
Source dataset
uspto-grants-1988_03
Patent number
US04734418

Reaction notes

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