Ethanol → 2,4-Dihydro-4-(4-piperidinyl)-3H-1,2,4-triazol-3-one

HRID 2217864Notes

Reaction equation

HRID 2217864 reaction equation
C1(C[N:8]2[CH2:13][CH2:12][CH:11]([N:14]3[CH:18]=[N:17][NH:16][C:15]3=[O:19])[CH2:10][CH2:9]2)C=CC=CC=1.C1CC=CCC=1.C(O)C>[OH-].[Pd+2].[OH-].O>[NH:8]1[CH2:9][CH2:10][CH:11]([N:14]2[CH:18]=[N:17][NH:16][C:15]2=[O:19])[CH2:12][CH2:13]1

Participants

6

Reactant 3

HCID 702EthanolHCID 123431,4-CyclohexadieneHCID 591757344-(1-Benzyl-4-piperidinyl)-3,4-dihydro-2H-1,2,4-triazole-3-one

Product 1

HCID 685022022,4-Dihydro-4-(4-piperidinyl)-3H-1,2,4-triazol-3-oneYield 50.3%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

2,4-Dihydro-4-[1-(phenylmethyl)-4-piperidinyl]-3H-1,2,4-triazol-3-one (Example 64(b)) (2.2 g) was divided between 2, 10 mL vials. 1,4-Cyclohexadiene (5 mL) and palladium hydroxide (270 mg, 20 wt. % on carbon) were added to each vial and the reactions were heated at 100° C. for 30 minutes within a microwave. The reaction mixtures were combined, ethanol (50 mL) and water (50 mL) were added and the mixture was filtered through diatomaceous earth and evaporated to give the sub-title compound as a solid (720 mg).

Workup

  1. customThe reaction mixtures
  2. filtrationthe mixture was filtered through diatomaceous earth
  3. customevaporated

Sources & evidence

ORD record
ord-64fb7b54e25f48c6b0e8d4b12a465203
Source dataset
uspto-grants-2008_08
Patent number
US07408065B2

Reaction notes

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