1-(3-(Trifluoromethyl)phenyl)piperazine → HCID 76283889, compound

HRID 1482612Notes

Reaction equation

HRID 1482612 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[CH:7][C:8]2[N:12]=[N:11][N:10]([CH2:13][CH2:14][CH2:15][CH2:16]Cl)[C:9]=2[CH:18]=1)=[O:4].[F:19][C:20]([F:34])([F:33])[C:21]1[CH:22]=[C:23]([N:27]2[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]2)[CH:24]=[CH:25][CH:26]=1.C(N(C(C)C)CC)(C)C.[I-].[K+]>C(#N)C>[CH3:1][O:2][C:3]([C:5]1[CH:6]=[CH:7][C:8]2[N:12]=[N:11][N:10]([CH2:13][CH2:14][CH2:15][CH2:16][N:30]3[CH2:29][CH2:28][N:27]([C:23]4[CH:24]=[CH:25][CH:26]=[C:21]([C:20]([F:33])([F:34])[F:19])[CH:22]=4)[CH2:32][CH2:31]3)[C:9]=2[CH:18]=1)=[O:4]

Participants

6

Reactant 4

HCID 42961-(3-(Trifluoromethyl)phenyl)piperazineHCID 4875Potassium IodideHCID 81531DiisopropylethylamineHCID 118386921HCID 118386921, compound

Product 1

HCID 76283889HCID 76283889, compoundYield 63.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

6-methoxycarbonyl-1-(4-chlorobutyl)-1H-benzotriazole (9.61 g, 0.036 mol) was dissolved into 100 ml of acetonitrile, 3-trifluoro methylphenylpiperazine (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 and mixed, then heated and refluxed to react for 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 and purified, eluted with dichloromethane to produce 8.8 g compound (I-56) with a yield of 63.4%. ESI-MS [M+H]+: m/z 461.2.

Workup

  1. additionwere respectively added
  2. additionmixed
  3. temperatureheated
  4. temperaturerefluxed
  5. customto react for 15 hours
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated
  8. customto produce oily products
  9. additiontreated by chromatography with neutral Al2O3
  10. custompurified
  11. washeluted with dichloromethane

Sources & evidence

ORD record
ord-f0e5bfada7fc472a99ad946fc94d77d2
Source dataset
uspto-grants-2016_08
Patent number
US09415047B2

Reaction notes

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