Iodoethane → 1-Ethylpiperidine-2,4-dione

HRID 977939Notes

Reaction equation

HRID 977939 reaction equation
[H-].[Na+].C[O:4][C:5]1[CH2:10][CH2:9][NH:8][C:7](=[O:11])[CH:6]=1.[CH2:12](I)[CH3:13]>CN(C)C=O>[CH2:12]([N:8]1[CH2:9][CH2:10][C:5](=[O:4])[CH2:6][C:7]1=[O:11])[CH3:13]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 136065754-methoxy-5,6-dihydro-2(1H)-pyridone

Product 1

HCID 137841191-Ethylpiperidine-2,4-dioneYield 78%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Sodium hydride (in the form of a 60% dispersion in oil) (447 mg) is suspended in N,N-dimethylformamide (10 ml), and thereto is added dropwise a solution of 4-methoxy-5,6-dihydro-2(1H)-pyridone (1.29 g) in N,N-dimethylformamide (30 ml). The mixture is stirred under ice-cooling for 30 minutes, and thereto is added dropwise ethyl iodide (0.97 ml). The mixture is stirred under ice-cooling for 30 minutes and further at room temperature for 2.5 hours. The reaction mixture is poured onto water and extracted with chloroform. The extract is washed with a saturated sodium chloride solution and dried. After evaporating the solvent, the residue is dissolved in ethanol (120 ml) and thereto is added 10% hydrochloric acid (60 ml), and the mixture is allowed to stand at 25° C. for 5 hours. After distilling off the solvent under reduced pressure, the residue is dissolved in chloroform, washed with 5% aqueous sodium hydrogen carbonate solution and water, and then dried. The solvent is distilled off to give 1-ethyl-2,4-dioxopiperidine (1.12 g, 78%).

Workup

  1. temperaturecooling for 30 minutes
  2. stirringThe mixture is stirred under ice-
  3. additionThe reaction mixture is poured onto water
  4. extractionextracted with chloroform
  5. washThe extract is washed with a saturated sodium chloride solution
  6. customdried
  7. customAfter evaporating the solvent
  8. dissolutionthe residue is dissolved in ethanol (120 ml)
  9. additionis added 10% hydrochloric acid (60 ml)
  10. distillationAfter distilling off the solvent under reduced pressure
  11. dissolutionthe residue is dissolved in chloroform
  12. washwashed with 5% aqueous sodium hydrogen carbonate solution and water
  13. customdried
  14. distillationThe solvent is distilled off

Sources & evidence

ORD record
ord-1b9f5830a6bd4b39b57e6d77b7a6a882
Source dataset
uspto-grants-1987_05
Patent number
US04663319

Reaction notes

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