Methanol → HCID 20204026, compound

HRID 977943Notes

Reaction equation

HRID 977943 reaction equation
COC(=O)[CH2:4][CH2:5][NH:6][CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[CH2:16]=[C:17]1[O:21][C:19](=[O:20])[CH2:18]1.[CH3:22][OH:23]>>[CH2:7]([N:6]1[CH2:5][CH2:4][C:22](=[O:23])[CH:18]([C:17](=[O:21])[CH3:16])[C:19]1=[O:20])[CH2:8][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 12661DiketeneHCID 9794284HCID 9794284, compound

Product 1

HCID 20204026HCID 20204026, compoundYield 95%

Procedure

N-Phenethyl-β-alanine methyl ester (80.2 g) is dissolved in methanol (150 ml), and thereto is added dropwise diketene (32 ml) under ice-cooling. The mixture is stirred at room temperature for 1 hour and then distilled to remove the solvent. The residue is dissolved in methanol (100 ml), and the solution is added dropwise to a solution of sodium methoxide [prepared from metal sodium (9.8 g) and methanol (150 ml)], and the mixture is stirred at room tempeature for 2 hours. After the reaction, the solvent is distilled off, and to the residue is added ice-water. The mixture is extracted with ethyl acetate, and the aqueous layer is acidified with conc. hydrochloric acid and then is extracted with ethyl acetate. The ethyl acetate extract is washed with water, dried and then distilled to remove the solvent to give 1-phenethyl-3-acetyl-2,4-dioxopiperidine (95.3 g, 95%) as a colorless oily substance.

Workup

  1. temperaturecooling
  2. distillationdistilled
  3. customto remove the solvent
  4. dissolutionThe residue is dissolved in methanol (100 ml)
  5. additionthe solution is added dropwise to a solution of sodium methoxide [prepared from metal sodium (9.8 g) and methanol (150 ml)]
  6. stirringthe mixture is stirred at room tempeature for 2 hours
  7. customAfter the reaction
  8. distillationthe solvent is distilled off
  9. additionto the residue is added ice-water
  10. extractionThe mixture is extracted with ethyl acetate
  11. extractionis extracted with ethyl acetate
  12. extractionThe ethyl acetate extract
  13. washis washed with water
  14. customdried
  15. distillationdistilled
  16. customto remove the solvent

Sources & evidence

ORD record
ord-05f2b272272c405598ca0674b2d02aef
Source dataset
uspto-grants-1987_05
Patent number
US04663319

Reaction notes

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