3-(Morpholinosulfonyl)pyridine → 591780-31-3

HRID 489902Notes

Reaction equation

HRID 489902 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([S:7]([N:10]2[CH2:15][CH2:14][O:13][CH2:12][CH2:11]2)(=[O:9])=[O:8])[CH:2]=1>C(O)C.O.[Pt](=O)=O>[NH:1]1[CH2:6][CH2:5][CH2:4][CH:3]([S:7]([N:10]2[CH2:11][CH2:12][O:13][CH2:14][CH2:15]2)(=[O:8])=[O:9])[CH2:2]1

Participants

5

Reactant 1

HCID 42764363-(Morpholinosulfonyl)pyridine

Product 1

HCID 22263137591780-31-3Yield 22.2%

Reagents, catalysts & solvents 3

HCID 345198Adams' catalystCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

4-(Pyridine-3-sulfonyl)-morpholine (25 mmol, 5.7 g) was shaken with platinum (IV) oxide (500 mg) in ethanol (50 mL) at 60° C. under hydrogen at 50 psi for 16 h. Reduction was incomplete so the catalyst was removed by filtration, the solvent evaporated under vacuum and the residue dissolved in a mixture of water (50 mL) and acetic acid (10 mL) with warming. Platinum (IV) oxide (1 g) was added and hydrogenation at 50 psi was continued for a further 70 h at 60° C. The catalyst was removed by filtration and the solvent was evaporated under vacuum to give an orange gum which was redissolved in water and the solution (pH 4-5) was extracted with dichloromethane (×3). The aqueous layer was evaporated to a small volume under vacuum, made strongly basic by the addition of 4 M sodium hydroxide solution, xylenes were added and the solvents were removed under vacuum. The residue was agitated with dichloromethane and anhydrous sodium sulfate, the solids removed by flitration through Celite® and the filtrate evaporated under vacuum to give 4-(piperidine-3-sulfonyl)-morpholine as a waxy orange solid (1.3 g, 22%).

Workup

  1. customwas removed by filtration
  2. customthe solvent evaporated under vacuum
  3. dissolutionthe residue dissolved in a mixture of water (50 mL) and acetic acid (10 mL)
  4. temperaturewith warming
  5. additionPlatinum (IV) oxide (1 g) was added
  6. customThe catalyst was removed by filtration
  7. customthe solvent was evaporated under vacuum
  8. customto give an orange gum which
  9. extractionthe solution (pH 4-5) was extracted with dichloromethane (×3)
  10. customThe aqueous layer was evaporated to a small volume under vacuum
  11. additionmade strongly basic by the addition of 4 M sodium hydroxide solution, xylenes
  12. additionwere added
  13. customthe solvents were removed under vacuum
  14. customthe solids removed by flitration through Celite®
  15. customthe filtrate evaporated under vacuum

Sources & evidence

ORD record
ord-f9ee5efa8e46412e8e6ea7a9b818307c
Source dataset
uspto-grants-2005_12
Patent number
US06979741B2

Reaction notes

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