Methanol → 4-(4-Piperidyl)pyridine

HRID 1662637Notes

Reaction equation

HRID 1662637 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[CH:12]=[CH:11][N:10]=[CH:9][CH:8]=2)=[CH:3][CH:2]=1.[H][H].CO>Cl.[Pt]=O>[NH:10]1[CH2:11][CH2:12][CH:7]([C:4]2[CH:3]=[CH:2][N:1]=[CH:6][CH:5]=2)[CH2:8][CH2:9]1

Participants

6

Reactant 3

HCID 887MethanolHCID 111074,4'-BipyridineHCID 178418361HCID 178418361, compound3×

Product 1

HCID 11395974-(4-Piperidyl)pyridineYield 7.5%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)Catalyst3×HCID 313Hydrochloric AcidSolvent

Procedure

To a solution of 5.00 g of 4,4′-bipyridine in 1 mol/L hydrochloric acid (32 ml) was added 299 mg of platinum oxide, and the reaction mixture was stirred under the conditions of 3.0 atm hydrogen and at 70° C. external temperature. After 3 hours, the solution was under ordinary temperature and ordinary pressure, then, 201 mg of platinum oxide was further added and the reaction was carried out under the conditions of 3.0 atm hydrogen and at 70° C. external temperature. After 4.5 hours, the solution was left to unattended for 16 hours in a state returned to under ordinary temperature and ordinary pressure. MeOH (30 ml) and 483 mg of platinum oxide were further added, and the mixture was stirred under the conditions of 3.0 atm hydrogen and 70° C. external temperature. The solution was stirred for 4 hours, then, filtered with celite, and the solvent of the filtrate was evaporated under reduced pressure. Then, a saturated aqueous solution of NaHCO3 was added to the solution and the resulting mixture was extracted with a mixed solvent of CHCl3:MeOH (10:1). The organic layer was evaporated under reduced pressure. Again, water was added to the solution, extracted with a mixed solvent of CHCl3:MeOH (10:1), and the organic layer was evaporated under reduced pressure. The precipitated solid was washed with water and dried to obtain 390 mg of the title compound (colorless amorphous).

Workup

  1. waitAfter 4.5 hours
  2. waitthe solution was left to unattended for 16 hours in a state
  3. filtrationfiltered with celite
  4. customthe solvent of the filtrate was evaporated under reduced pressure
  5. additionThen, a saturated aqueous solution of NaHCO3 was added to the solution
  6. extractionthe resulting mixture was extracted with a mixed solvent of CHCl3:MeOH (10:1)
  7. customThe organic layer was evaporated under reduced pressure
  8. additionAgain, water was added to the solution
  9. extractionextracted with a mixed solvent of CHCl3:MeOH (10:1)
  10. customthe organic layer was evaporated under reduced pressure
  11. washThe precipitated solid was washed with water
  12. customdried

Sources & evidence

ORD record
ord-b194d70a668541edaa6a2e59ebc2a073
Source dataset
uspto-grants-2011_10
Patent number
US08030499B2

Reaction notes

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