Sodium → Methyl 1-(3-pyridylmethyl)-2,4-dioxopiperidine-3-carboxylate

HRID 977964Notes

Reaction equation

HRID 977964 reaction equation
[Na].[N:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH2:8][N:9]([CH2:18][CH2:19][C:20]([O:22]C)=O)[C:10]([CH2:12][C:13]([O:15][CH2:16]C)=[O:14])=[O:11])[CH:3]=1>CO.C1C=CC=CC=1>[N:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH2:8][N:9]2[CH2:18][CH2:19][C:20](=[O:22])[CH:12]([C:13]([O:15][CH3:16])=[O:14])[C:10]2=[O:11])[CH:3]=1

Participants

5

Reactant 2

HCID 5360545SodiumHCID 53944986Ethyl[N-(3-pyridylmethyl)-N-(methoxycarbonylethyl)carbamoyl]acetate

Product 1

HCID 20204023Methyl 1-(3-pyridylmethyl)-2,4-dioxopiperidine-3-carboxylateYield 99.9%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 887MethanolSolvent

Procedure

Sodium (0.77 g) is dissolved in methanol (30 ml), and thereto is added dropwise a solution of ethyl [N-(3-pyridylmethyl)-N-(methoxycarbonylethyl)carbamoyl]acetate (10.0 g) in benzene (170 ml) at 3°-8° C. The mixture is stirred at the same meperature for 2 hours. The mixture is distilled to remove the solvent, and the residue is dissolved in water. The aqueous solution is extracted with benzene, and the aqueous layer is neutralized with 10% HCl, and extracted with chloroform. The extract is dried and distilled to remove the solvent to give methyl 1-(3-pyridylmethyl)-2,4-dioxopiperidine-3-carboxylate (8.50 g, quantitative) as oil.

Workup

  1. distillationThe mixture is distilled
  2. customto remove the solvent
  3. dissolutionthe residue is dissolved in water
  4. extractionThe aqueous solution is extracted with benzene
  5. extractionextracted with chloroform
  6. customThe extract is dried
  7. distillationdistilled
  8. customto remove the solvent

Sources & evidence

ORD record
ord-3c8b492233f447a5b3d01e1f05db6dd9
Source dataset
uspto-grants-1987_05
Patent number
US04663319

Reaction notes

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