Triethylamine → 1-(Pyridin-4-yl)piperidin-4-one

HRID 412602Notes

Reaction equation

HRID 412602 reaction equation
Cl.Cl[C:3]1[CH:8]=[CH:7][N:6]=[CH:5][CH:4]=1.[O:9]=[C:10]1C2(CCNCC2)C(=O)CC1.C([N:23]([CH2:26][CH3:27])[CH2:24][CH3:25])C>C(O)C.O>[N:6]1[CH:7]=[CH:8][C:3]([N:23]2[CH2:24][CH2:25][C:10](=[O:9])[CH2:27][CH2:26]2)=[CH:4][CH:5]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 818524-Chloropyridine hydrochlorideHCID 2880631,4-Dioxo-8-azaspiro[4,5]decane

Product 1

HCID 113327931-(Pyridin-4-yl)piperidin-4-one

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
150 °C

Procedure

A solution of 4-chloropyridine hydrochloride (10 g), 1,4-dioxo-8-azaspiro[4,5]decane (10 g) and triethylamine (29 ml) in a mixture of ethanol (10 ml) and water (30 ml) was stirred at 150° C. for 22 hours in a sealed tube. After completion of the reaction, the solvent was evaporated and 5N aqueous sodium hydroxide solution (25 ml) was added. The mixture was extracted with a mixed solvent of chloroform-methanol (10:1). The organic layer was dried over anhydrous sodium sulfate and the solvent was evaporated. To the obtained residue was dropwise added conc. hydrochloric acid (30 ml) with ice-cooling, and the mixture was stirred at the same temperature for 10 min. After completion of the reaction, sodium hydroxide (15 g) was added. The mixture was extracted with chloroform and dried over anhydrous sodium sulfate. The solvent was evaporated and the obtained residue was purified by silica gel column chromatography (chloroform:methanol=9:1, 1% aqueous ammonia) and dried under reduced pressure to give the title compound (6.1 g).

Workup

  1. customAfter completion of the reaction
  2. customthe solvent was evaporated
  3. addition5N aqueous sodium hydroxide solution (25 ml) was added
  4. extractionThe mixture was extracted with a mixed solvent of chloroform-methanol (10:1)
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. customthe solvent was evaporated
  7. temperaturecooling
  8. stirringthe mixture was stirred at the same temperature for 10 min
  9. customAfter completion of the reaction, sodium hydroxide (15 g)
  10. additionwas added
  11. extractionThe mixture was extracted with chloroform
  12. dry with materialdried over anhydrous sodium sulfate
  13. customThe solvent was evaporated
  14. customthe obtained residue was purified by silica gel column chromatography (chloroform:methanol=9:1, 1% aqueous ammonia)
  15. customdried under reduced pressure

Sources & evidence

ORD record
ord-4c0a10a26df141188e43423e50e0c92d
Source dataset
uspto-grants-2003_05
Patent number
US06562828B1

Reaction notes

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