Acetic Acid → ethyl 2,6-dioxopiperidine-3-carboxylate

HRID 483110Notes

Reaction equation

HRID 483110 reaction equation
[C:1]([O:9]CC)(=O)[CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].[H-].[Na+].[C:14]([NH2:18])(=[O:17])[CH:15]=[CH2:16].C(O)(=O)C>O1CCCC1.C(OCC)(=O)C>[CH2:6]([O:5][C:3]([CH:2]1[CH2:16][CH2:15][C:14](=[O:17])[NH:18][C:1]1=[O:9])=[O:4])[CH3:7]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 6579AcrylamideHCID 7761Diethyl MalonateHCID 24758Sodium hydride

Product 1

HCID 300155ethyl 2,6-dioxopiperidine-3-carboxylate

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of diethyl malonate (2.3 ml) in tetrahydrofuran (2.3 ml) cooled at 0° C. is added sodium hydride (400 mg). After stirring for 10 minutes, the mixture is mixed with acrylamide (710 mg) and let react at 0° C. for 70 minutes and at room temperature for 3.5 hours. The mixture is mixed with acetic acid (0.7 ml), stirred for 20 minutes, diluted with ethyl acetate, filtered to remove solid, concentrated, and triturated in n-hexane to afford 2,6-dioxo-piperidine-3-carboxylic acid ethyl ester (1.18 g). m.p. 69°-74° C.

Workup

  1. customlet react at 0° C. for 70 minutes and at room temperature for 3.5 hours
  2. stirringstirred for 20 minutes
  3. filtrationfiltered
  4. customto remove solid
  5. concentrationconcentrated
  6. customtriturated in n-hexane

Sources & evidence

ORD record
ord-48624da71a47416c91af1405c5bcaad1
Source dataset
uspto-grants-1986_03
Patent number
US04578378

Reaction notes

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