1-(3-(Trifluoromethyl)phenyl)piperazine → HCID 90182593, compound

HRID 1482616Notes

Reaction equation

HRID 1482616 reaction equation
Cl[CH2:2][CH2:3][CH2:4][N:5]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[CH:7]=[N:6]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(N(C(C)C)CC)(C)C.[I-].[K+]>C(#N)C>[F:29][C:15]([F:14])([F:28])[C:16]1[CH:17]=[C:18]([N:22]2[CH2:27][CH2:26][N:25]([CH2:2][CH2:3][CH2:4][N:5]3[C:9]4[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=4[CH:7]=[N:6]3)[CH2:24][CH2:23]2)[CH:19]=[CH:20][CH:21]=1

Participants

6

Reactant 4

HCID 42961-(3-(Trifluoromethyl)phenyl)piperazineHCID 4875Potassium IodideHCID 81531DiisopropylethylamineHCID 22239044HCID 22239044, compound

Product 1

HCID 90182593HCID 90182593, compoundYield 65.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1-(3-chloropropyl)-1H-benzopyrazole (6.98 g, 0.036 mol) was dissolved into 100 ml of acetonitrile, 3-trifluoromethyl phenyl piperazine (6.9 g, 0.03 mol), diisopropylethylamine (15.5 g, 0.12 mol) and potassium iodide (5.0 g, 0.03 mol) were respectively added. The mixture was stirred for 10 min at ambient temperature, and then heated and refluxed to react for 10-15 hours. The mixture was cooled down to ambient temperature and filtered. The filtrate was concentrated to produce oily products, and treated by chromatography with neutral Al2O3, eluted with dichloromethane/methanol mixture to produce 7.6 g compound (I-59) with a yield of 63.1%. ESI-MS [M+H]+: m/z 389.2.

Workup

  1. additionwere respectively added
  2. temperatureheated
  3. temperaturerefluxed
  4. customto react for 10-15 hours
  5. temperatureThe mixture was cooled down to ambient temperature
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated
  8. customto produce oily products
  9. additiontreated by chromatography with neutral Al2O3
  10. washeluted with dichloromethane/methanol mixture

Sources & evidence

ORD record
ord-84df68ece57f4a9aa642e42b803bf326
Source dataset
uspto-grants-2016_08
Patent number
US09415047B2

Reaction notes

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