Water → (+/-)-2-(1-ethyl-2-oxopropyl)-2,4-dihydro-4-[4-[4-(4-methoxyphenyl)-1-piperazinyl]phenyl]-3H-1,2,4-triazol-3-one

HRID 1279203

Reaction equation

HRID 1279203 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH2:14][CH2:13][N:12]([C:15]3[CH:20]=[CH:19][C:18]([N:21]4[CH:25]=[N:24][NH:23][C:22]4=[O:26])=[CH:17][CH:16]=3)[CH2:11][CH2:10]2)=[CH:5][CH:4]=1.Br[CH:28]([CH2:32][CH3:33])[C:29](=[O:31])[CH3:30].C([O-])([O-])=O.[K+].[K+].O>CN(C=O)C.C1(C)C=CC=CC=1>[CH2:32]([CH:28]([N:23]1[C:22](=[O:26])[N:21]([C:18]2[CH:19]=[CH:20][C:15]([N:12]3[CH2:11][CH2:10][N:9]([C:6]4[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=4)[CH2:14][CH2:13]3)=[CH:16][CH:17]=2)[CH:25]=[N:24]1)[C:29](=[O:31])[CH3:30])[CH3:33]

Participants

7

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 42465972,4-Dihydro-4-(4-(4-(4-methoxyphenyl)piperazin-1-yl)phenyl)-3H-1,2,4-triazol-3-oneHCID 100122493-Bromo-2-pentanone

Product 1

HCID 18427435(+/-)-2-(1-ethyl-2-oxopropyl)-2,4-dihydro-4-[4-[4-(4-methoxyphenyl)-1-piperazinyl]phenyl]-3H-1,2,4-triazol-3-oneYield 21.1%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 2,4-dihydro-4-[4-[4-(4-methoxyphenyl)-1-piperazinyl]phenyl]-3H-1,2,4-triazol-3-one (0.05 mol) prepared as described in Eβ-A-0,006,711, 3-bromo-2-pentanone (0.073 mol) and K2CO3 (10 g) in DMF (200 ml) and toluene (200 ml) was stirred and refluxed overnight using a water separator. The solvent was evaporated. The residue was dissolved in CH2Cl2. The organic solution was washed, dried, filtered and the solvent was evaporated. The residue was crystallized from 2-propanol. The precipitate was filtered off and the filtrate was evaporated. The residue was triturated in DIPE, filtered off and dried, yielding 4.6 g of (±)-2-(1-ethyl-2-oxopropyl)-2,4-dihydro-4-[4-[4-(4-methoxyphenyl)-1-piperazinyl]phenyl]-3H-1,2,4-triazol-3-one (intermn.

Workup

  1. customprepared
  2. temperaturerefluxed overnight
  3. customThe solvent was evaporated
  4. dissolutionThe residue was dissolved in CH2Cl2
  5. washThe organic solution was washed
  6. customdried
  7. filtrationfiltered
  8. customthe solvent was evaporated
  9. customThe residue was crystallized from 2-propanol
  10. filtrationThe precipitate was filtered off
  11. customthe filtrate was evaporated
  12. customThe residue was triturated in DIPE
  13. filtrationfiltered off
  14. customdried

Sources & evidence

ORD record
ord-d735e7da143a40f9a2b03387c6a71269
Source dataset
uspto-grants-2002_09
Patent number
US06448244B1

Linked notes

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