Chloroacetone → 2,4dihydro-4-[4-[4-(4-methoxy-phenyl)-1-piperazinyl]phenyl]-2-(2-oxopropyl)-3H-1,2,4-triazol-3-one

HRID 1934584Notes

Reaction equation

HRID 1934584 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([N:11]2[CH2:16][CH2:15][N:14]([C:17]3[CH:22]=[CH:21][C:20]([N:23]4[CH:27]=[N:26][NH:25][C:24]4=[O:28])=[CH:19][CH:18]=3)[CH2:13][CH2:12]2)=[CH:7][CH:6]=1.Cl[CH2:30][C:31](=[O:33])[CH3:32]>CN(C=O)C>[CH3:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([N:11]2[CH2:12][CH2:13][N:14]([C:17]3[CH:22]=[CH:21][C:20]([N:23]4[CH:27]=[N:26][N:25]([CH2:30][C:31](=[O:33])[CH3:32])[C:24]4=[O:28])=[CH:19][CH:18]=3)[CH2:15][CH2:16]2)=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 6571ChloroacetoneHCID 24758Sodium hydrideHCID 42465972,4-Dihydro-4-(4-(4-(4-methoxyphenyl)piperazin-1-yl)phenyl)-3H-1,2,4-triazol-3-one

Product 1

HCID 224664582,4dihydro-4-[4-[4-(4-methoxy-phenyl)-1-piperazinyl]phenyl]-2-(2-oxopropyl)-3H-1,2,4-triazol-3-oneYield 1.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
50 °C

Procedure

Reaction under N2 atmosphere. NaH 60% (0.12 mol) was added to 2,4-dihydro-4-[4-[4-(4-methoxyphenyl)-1-piperazinyl]phenyl]-3H-1,2,4-triazol-3-one (0.1 mol) in DMF, and stirred for 30 minutes at 50° C. A solution of 1-chloro-2-propanone (0.1 mol) in DMF was added dropwise and the resulting reaction mixture was stirred overnight at 50° C. The reaction mixture was cooled, poured out into ice-water and the resulting precipitate was filtered off, washed with water, and dried. This fraction was recrystallized from CH2Cl2/CH3OH. The precipitate was filtered off and the filtrate was evaporated. The residue was crystallized from methanol, filtered off and dried. The residue was combined with the crystallized compound, recrystallized from CH2Cl2/CH3OH, filtered off and dried, yielding 0.65 g of 2,4dihydro-4-[4-[4-(4-methoxy-phenyl)-1-piperazinyl]phenyl]-2-(2-oxopropyl)-3H-1,2,4-triazol-3-one (interm. 20).

Workup

  1. customReaction under N2 atmosphere
  2. customthe resulting reaction mixture
  3. stirringwas stirred overnight at 50° C
  4. temperatureThe reaction mixture was cooled
  5. filtrationthe resulting precipitate was filtered off
  6. washwashed with water
  7. customdried
  8. customThis fraction was recrystallized from CH2Cl2/CH3OH
  9. filtrationThe precipitate was filtered off
  10. customthe filtrate was evaporated
  11. customThe residue was crystallized from methanol
  12. filtrationfiltered off
  13. customdried
  14. customrecrystallized from CH2Cl2/CH3OH
  15. filtrationfiltered off
  16. customdried

Sources & evidence

ORD record
ord-8d274a7dff8649a5920520a9158da51b
Source dataset
uspto-grants-2002_05
Patent number
US06384030B1

Reaction notes

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