Water → HCID 20204039, compound

HRID 977970Notes

Reaction equation

HRID 977970 reaction equation
[Na].[CH2:2]([O:4][C:5](=[O:26])[CH2:6][C:7](=[O:25])[N:8]([CH2:15][C:16]1[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[CH:18][CH:17]=1)[CH2:9][CH2:10][C:11]([O:13]C)=O)[CH3:3].O>C(O)C.C1C=CC=CC=1>[N+:22]([C:19]1[CH:20]=[CH:21][C:16]([CH2:15][N:8]2[CH2:9][CH2:10][C:11](=[O:13])[CH:6]([C:5]([O:4][CH2:2][CH3:3])=[O:26])[C:7]2=[O:25])=[CH:17][CH:18]=1)([O-:24])=[O:23]

Participants

6

Reactant 3

HCID 962WaterHCID 5360545SodiumHCID 131715121HCID 131715121, compound

Product 1

HCID 20204039HCID 20204039, compoundYield 88.4%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 702EthanolSolvent

Procedure

Sodium (690 mg) is dissolved in ethanol (25 ml), and thereto is added dropwise a solution of ethyl[N-(p-nitrobenzyl)-N-(methoxycarbonylethyl)carbamoyl]acetate (10.0 g) in benzene (160 ml) at room temperature. The mixture was stirred at the same temperature for 1.5 hours. The mixture is poured into water. The aqueous layer is separated, neutralized with 10% HCl and extracted with ethyl acetate. The extract is washed with a saturated sodium chloride solution, dried and then distilled to remove the solvent to give ethyl 1-(p-nitrobenzyl)-2,4-dioxopiperidine-3-carboxylate (8.03 g, 88.4%) as yellow oil.

Workup

  1. customThe aqueous layer is separated
  2. extractionextracted with ethyl acetate
  3. washThe extract is washed with a saturated sodium chloride solution
  4. customdried
  5. distillationdistilled
  6. customto remove the solvent

Sources & evidence

ORD record
ord-f4abff14a7e14e178f13652387558400
Source dataset
uspto-grants-1987_05
Patent number
US04663319

Reaction notes

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