4-Aminopyridine → 1-(4-Pyridinyl)-2,6-piperidinedione

HRID 127272Notes

Reaction equation

HRID 127272 reaction equation
[C:1]1(=[O:8])[O:7][C:5](=O)[CH2:4][CH2:3][CH2:2]1.[NH2:9][C:10]1[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=1>C1(C)C(C)=CC=CC=1>[N:13]1[CH:14]=[CH:15][C:10]([N:9]2[C:1](=[O:8])[CH2:2][CH2:3][CH2:4][C:5]2=[O:7])=[CH:11][CH:12]=1

Participants

4

Reactant 2

HCID 17274-AminopyridineHCID 7940Glutaric anhydride

Product 1

HCID 128225471-(4-Pyridinyl)-2,6-piperidinedione

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

The starting material is prepared as follows: The mixture of 34.2 g of glutaric anhydride, 28.2 g of 4-aminopyridine and 650 ml of xylene is refluxed with stirring for 6 hours. It is allowed to cool to room temperature, the solids are filtered off and extracted twice with 200 ml chloroform at reflux. The combined extracts are evaporated and the residue recrystallized twice from ethyl acetate to yield the 1-(4-pyridyl)-piperidine-2,6-dione melting at 153°-155°.

Workup

  1. customThe starting material is prepared
  2. temperatureis refluxed
  3. filtrationthe solids are filtered off
  4. extractionextracted twice with 200 ml chloroform
  5. temperatureat reflux
  6. customThe combined extracts are evaporated
  7. customthe residue recrystallized twice from ethyl acetate

Sources & evidence

ORD record
ord-203c32a216f2412e8eb5164c292a0af3
Source dataset
uspto-grants-1981_03
Patent number
US04255429

Reaction notes

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