Diethyl Oxalate → 2,3-Dioxo-1-p-tolylpiperidine-4-carbonitrile

HRID 390000Notes

Reaction equation

HRID 390000 reaction equation
[C:1]1([CH3:13])[CH:6]=[CH:5][C:4]([NH:7][CH2:8][CH2:9][CH2:10][C:11]#[N:12])=[CH:3][CH:2]=1.[C:14]([O:21]CC)(=O)[C:15]([O:17]CC)=O.[O-]CC.[Na+]>C(O)C>[O:21]=[C:14]1[C:15](=[O:17])[CH:10]([C:11]#[N:12])[CH2:9][CH2:8][N:7]1[C:4]1[CH:3]=[CH:2][C:1]([CH3:13])=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 7268Diethyl OxalateHCID 2723922Sodium ethoxideHCID 213325214-(p-Tolylamino)butanenitrile

Product 1

HCID 679973142,3-Dioxo-1-p-tolylpiperidine-4-carbonitrileYield 51.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4-(p-Tolylamino)butanenitrile (13.23 g, 75.929 mmol) was dissolved in ethanol (189.8 mL). After adding diethyl oxalate (10.3 mL, 75.929 mmol) and then adding sodium ethoxide (34.0 mL, 91.115 mmol) to the resultant reaction mixture, reaction was carried out under reflux for 2 days. The reaction solution was cooled to room temperature and the concentrated solution was filtered. A target compound (8.94 g, 39.167 mmol, 51.6%) was yielded as yellow solid.

Workup

  1. temperatureunder reflux for 2 days
  2. filtrationthe concentrated solution was filtered

Sources & evidence

ORD record
ord-fa899f9e5bb540a9847758db1863c18e
Source dataset
uspto-grants-2013_02
Patent number
US08383631B2

Reaction notes

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