1-(3-(Trifluoromethyl)phenyl)piperazine → HCID 9931066, compound

HRID 2307846Notes

Reaction equation

HRID 2307846 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:12][N:11]=[C:10]([CH3:13])[N:9]=2)=[CH:4][CH:3]=1.[F:14][C:15]([F:29])([F:28])[C:16]1[CH:17]=[C:18]([N:22]2[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]2)[CH:19]=[CH:20][CH:21]=1.C(=O)([O-])[O-].[Na+].[Na+]>CN(C=O)C>[CH3:13][C:10]1[N:9]=[C:8]([C:5]2[CH:6]=[CH:7][C:2]([N:25]3[CH2:24][CH2:23][N:22]([C:18]4[CH:19]=[CH:20][CH:21]=[C:16]([C:15]([F:28])([F:29])[F:14])[CH:17]=4)[CH2:27][CH2:26]3)=[CH:3][CH:4]=2)[S:12][N:11]=1

Participants

5

Reactant 3

HCID 42961-(3-(Trifluoromethyl)phenyl)piperazineHCID 10340Sodium CarbonateHCID 10932319HCID 10932319, compound

Product 1

HCID 9931066HCID 9931066, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of 5-(4-fluorophenyl)-3-methyl-1,2,4-thiadiazole (0.012 mol), 1-[3-(trifluoromethyl)phenyl]-piperazine (0.014 mol) and sodium carbonate (0.024 mol) in DMF (10 ml) was stirred at 140° C. for 24 hours, then at 150° C. for 24 hours, cooled, poured out into ice water (200 ml) and stirred. The precipitate was filtered off, taken up in DCM, dried, filtered and the solvent was evaporated. The residue was crystallized from DIPE. The precipitate was filtered off and dried, yielding 2.5 g (52%) of 1-[4-(3-methyl-1,2,4-thiadiazol-5-yl)phenyl]-4-[3-(trifluoromethyl)phenyl]piperazine (compound 2).

Workup

  1. waitat 150° C. for 24 hours
  2. temperaturecooled
  3. stirringstirred
  4. filtrationThe precipitate was filtered off
  5. customdried
  6. filtrationfiltered
  7. customthe solvent was evaporated
  8. customThe residue was crystallized from DIPE
  9. filtrationThe precipitate was filtered off
  10. customdried

Sources & evidence

ORD record
ord-a78d18f122334fc3b82730f59a83dd7f
Source dataset
uspto-grants-2004_12
Patent number
US06833369B2

Reaction notes

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