4-Aminopyridine → 4-Phenyl-1-(4-pyridyl)-piperidin-2,6-dione

HRID 1105683Notes

Reaction equation

HRID 1105683 reaction equation
[C:1]1([CH:7]2[CH2:13][C:12](=[O:14])[O:11][C:9](=O)[CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:15][C:16]1[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=1.C1(C)C(C)=CC=CC=1.CS(O)(=O)=O>O>[C:1]1([CH:7]2[CH2:8][C:9](=[O:11])[N:15]([C:16]3[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=3)[C:12](=[O:14])[CH2:13]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 17274-AminopyridineHCID 6395Methanesulfonic AcidHCID 7237O-XyleneHCID 2978824-Phenyloxane-2,6-dione

Product 1

HCID 128225504-Phenyl-1-(4-pyridyl)-piperidin-2,6-dione

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The starting material is prepared as follows: The mixture of 19 g of 3-phenylglutaric anhydride, 10.3 g of 4-aminopyridine, 350 ml of xylene and 2.5 g of methane sulfonic acid is refluxed on a water separator while stirring for 2 days. The hot solution is decanted from some insolubles, cooled, filtered and the residue triturated with hot isopropanol, to yield the 4-phenyl-1-(4-pyridyl)-piperidin-2,6-dione melting at 229°-230°; the analogously prepared 4-(p-methoxyphenyl)-1-(4-pyridyl)-piperidine-2,6-dione melts at 168°-169°.

Workup

  1. customThe starting material is prepared
  2. customThe hot solution is decanted from some insolubles
  3. temperaturecooled
  4. filtrationfiltered
  5. customthe residue triturated with hot isopropanol

Sources & evidence

ORD record
ord-da4e9896a9004c0d8ef77ad2df359122
Source dataset
uspto-grants-1982_01
Patent number
US04309541

Reaction notes

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