Piperidine → HCID 59731969, compound

HRID 132212Notes

Reaction equation

HRID 132212 reaction equation
C([N:8]1[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[C:11](=[O:18])[CH2:10][S:9]1(=[O:20])=[O:19])C1C=CC=CC=1.[C:21]([O:25][C:26]([N:28]1[CH2:33][CH2:32][C:31](=O)[CH2:30][CH2:29]1)=[O:27])([CH3:24])([CH3:23])[CH3:22].N1CCCCC1.[H][H]>N1C=CC=CC=1>[C:21]([O:25][C:26]([N:28]1[CH2:33][CH2:32][CH:31]([CH:10]2[C:11](=[O:18])[C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[NH:8][S:9]2(=[O:19])=[O:20])[CH2:30][CH2:29]1)=[O:27])([CH3:24])([CH3:22])[CH3:23]

Participants

6

Reactant 4

HCID 8082PiperidineHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 2799884HCID 2799884, compoundHCID 178418361HCID 178418361, compound3×

Product 1

HCID 59731969HCID 59731969, compoundYield 24%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

1-Benzyl-2,2-dioxo-2,3-dihydro-1H-2,1-benzothiazin-4-one (1.51 g, 5.26 mmol) was dissolved in pyridine (50 mL). N-tert-Butoxycarbonyl-4-piperidinone (1.24 g, 6.33 mmol) was added to the mixture followed by piperidine (110 μL, 1.11 mmol). Molecular sieves were added to the mixture. Reaction stirred at room temperature for 40 hours. Reaction mixture was filtered over celite. Filtrate was concentrated in vacuo. Residue was purified by silica gel chromatography. The major component was isolated and the fractions concentrated in vacuo. Residue was dissolved in methanol (50 mL). A catalytic amount of 50% wet 10% palladium on carbon was added to the mixture. Reaction vessel was placed on a Parr apparatus and charged with 55 psi of hydrogen gas. Reaction shook at room temperature for 2 hours. Reaction mixture was filtered over celite. Fresh catalyst was added to the filtrate. Reaction vessel was placed on a Parr apparatus and charged with 55 psi of hydrogen gas. Reaction shook at room temperature for 1 hour. Mixture was filtered over celite. A third batch of fresh catalyst was added to the mixture. Reaction vessel was placed on a Parr apparatus and charged with 55 psi of hydrogen gas. Reaction shook at room temperature for 7.5 hours. Catalyst was filtered off. Filtrate was concentrated in vacuo. Silica gel chromatography afforded the title compound as pale yellow solid in 24% yield. MS m/e (M−H)−=379.1.

Workup

  1. additionMolecular sieves were added to the mixture
  2. customReaction
  3. customReaction mixture
  4. filtrationwas filtered over celite
  5. concentrationFiltrate was concentrated in vacuo
  6. customResidue was purified by silica gel chromatography
  7. customThe major component was isolated
  8. concentrationthe fractions concentrated in vacuo
  9. dissolutionResidue was dissolved in methanol (50 mL)
  10. additionA catalytic amount of 50% wet 10% palladium on carbon was added to the mixture
  11. customReaction vessel
  12. customReaction
  13. stirringshook at room temperature for 2 hours
  14. customReaction mixture
  15. filtrationwas filtered over celite
  16. additionFresh catalyst was added to the filtrate
  17. customReaction vessel
  18. customReaction
  19. stirringshook at room temperature for 1 hour
  20. filtrationMixture was filtered over celite
  21. additionA third batch of fresh catalyst was added to the mixture
  22. customReaction vessel
  23. customReaction
  24. stirringshook at room temperature for 7.5 hours
  25. filtrationCatalyst was filtered off
  26. concentrationFiltrate was concentrated in vacuo

Sources & evidence

ORD record
ord-a0b06d781c34484f90c2ded24578179c
Source dataset
uspto-grants-2008_06
Patent number
US07384930B2

Reaction notes

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