Piperidine → HCID 136147091, compound

HRID 466052Notes

Reaction equation

HRID 466052 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH:10]=[C:11]([C:14]([CH3:17])([CH3:16])[CH3:15])[C:12]=1[OH:13])C=O)([CH3:4])([CH3:3])[CH3:2].[O:18]=[C:19]1[NH:23][N:22]=[C:21]([CH2:24][C:25](O)=O)[NH:20]1.N1CCCCC1>N1C=CC=CC=1.C1(C)C=CC=CC=1>[CH3:2][C:1]([C:5]1[CH:6]=[C:7]([CH:25]=[CH:24][C:21]2[NH:20][C:19](=[O:18])[NH:23][N:22]=2)[CH:10]=[C:11]([C:14]([CH3:15])([CH3:16])[CH3:17])[C:12]=1[OH:13])([CH3:4])[CH3:3]

Participants

6

Reactant 3

HCID 8082PiperidineHCID 732193,5-Di-tert-butyl-4-hydroxybenzaldehydeHCID 135786545(5-Oxo-2,5-dihydro-1H-1,2,4-triazol-3-yl)acetic acid

Product 1

HCID 136147091HCID 136147091, compoundYield 40%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 1140TolueneSolvent

Procedure

A solution of 3,5-di-t-butyl-4-hydroxybenzaldehyde (3.5 g, 15 mmol), 2-(5-oxo-4,5-dihydro-1H-1,2,4-triazol-3-yl) acetic acid (N. W. Jacobsen, B. L. McCarthy, and S. Smith, Aust. J. Chem., 32 161-5 (1979] (2.15 g, 15 mmol), and piperidine (1.3 g, 15 mmol) in pyridine (15 ml) and toluene (45 ml) is heated at reflux (with removal of water) for 40 hours. The reaction mixture is cooled, filtered, and evaporated. The residue is partitioned between ethyl acetate (100 ml) and 1N HCl (400 ml). The organic layer is washed two additional times with 1N HCl (400 ml) and then is dried (MgSO4) and evaporated. The residue crystallized upon addition of hot dichloromethane. Recrystallization from isopropyl ether/ethyl acetate gives 5-[2-[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]ethenyl]-2,4-dihydro-3H-1,2,4-triazol-3-one (2.49 g, 40%), mp 280°-284° C.

Workup

  1. temperatureat reflux
  2. custom(with removal of water) for 40 hours
  3. temperatureThe reaction mixture is cooled
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue is partitioned between ethyl acetate (100 ml) and 1N HCl (400 ml)
  7. washThe organic layer is washed two additional times with 1N HCl (400 ml)
  8. dry with materialis dried (MgSO4)
  9. customevaporated
  10. customThe residue crystallized upon addition of hot dichloromethane
  11. customRecrystallization from isopropyl ether/ethyl acetate

Sources & evidence

ORD record
ord-2797e438ca96465dab0f37781e3ac3d3
Source dataset
uspto-grants-1992_10
Patent number
US05155122

Reaction notes

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