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

HRID 1105684Notes

Reaction equation

HRID 1105684 reaction equation
[C:1]1([CH:7]2[CH2:12][C:11](=[O:13])[N:10]([C:14]3[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=3)[C:9](=[O:20])[CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>[Pd].C(O)(=O)C>[C:1]1([CH:7]2[CH2:8][C:9](=[O:20])[N:10]([CH:14]3[CH2:15][CH2:16][NH:17][CH2:18][CH2:19]3)[C:11](=[O:13])[CH2:12]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 1

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

Product 1

HCID 128225644-Phenyl-1-(4-piperidinyl)-piperidin-2,6-dione

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

The mixture of 14.6 g of 4-phenyl-1-(4-pyridyl)-piperidin-2,6-dione, 12.3 g of 10% palladium on carbon and 200 ml of glacial acetic acid is hydrogenated at 1.7 atm. and 100° for 8 hours. After cooling, the mixture is filtered, evaporated, the residue dissolved in the minimum amount of water and the solution basified with sodium carbonate. It is extracted with ethyl acetate, the extract evaporated and the residue crystallized by trituration with 75 ml of diethyl ether-hexane (3:1) and recrystallized from 50 ml of isopropanol to yield the 4-phenyl-1-(4-piperidinyl)-piperidin-2,6-dione melting at 182°-189°; its p-methoxyphenyl analog melts at 127°-129°.

Workup

  1. temperatureAfter cooling
  2. filtrationthe mixture is filtered
  3. customevaporated
  4. dissolutionthe residue dissolved in the minimum amount of water
  5. extractionIt is extracted with ethyl acetate
  6. customthe extract evaporated
  7. customthe residue crystallized by trituration with 75 ml of diethyl ether-hexane (3:1)
  8. customrecrystallized from 50 ml of isopropanol

Sources & evidence

ORD record
ord-94f703fb9a204fecbefa14b9570e20da
Source dataset
uspto-grants-1982_01
Patent number
US04309541

Reaction notes

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