Potassium Iodide → N-(4-(1H-benzotriazole-1-yl)butyl)-4-(3-trifluoromethylphenyl)piperidine

HRID 1482647Notes

Reaction equation

HRID 1482647 reaction equation
F[C:2]1[CH:3]=[CH:4][C:5]2[N:9]=[N:8][N:7]([CH2:10][CH2:11][CH2:12][CH2:13]Cl)[C:6]=2[CH:15]=1.[F:16][C:17]([F:31])([F:30])[C:18]1[CH:19]=[C:20]([CH:24]2[CH2:29][CH2:28]CN[CH2:25]2)[CH:21]=[CH:22][CH:23]=1.[CH:32]([N:35](C(C)C)CC)(C)C.[I-].[K+]>C(#N)C>[N:7]1([CH2:10][CH2:11][CH2:12][CH2:13][N:35]2[CH2:32][CH2:25][CH:24]([C:20]3[CH:21]=[CH:22][CH:23]=[C:18]([C:17]([F:16])([F:30])[F:31])[CH:19]=3)[CH2:29][CH2:28]2)[C:6]2[CH:15]=[CH:2][CH:3]=[CH:4][C:5]=2[N:9]=[N:8]1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 81531DiisopropylethylamineHCID 30490313-[3-(Trifluoromethyl)phenyl]piperidineHCID 1183869061-(4-chlorobutyl)-6-fluoro-1H-benzotriazole

Product 1

HCID 76280853N-(4-(1H-benzotriazole-1-yl)butyl)-4-(3-trifluoromethylphenyl)piperidineYield 67.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

6-fluoro-1-(4-chlorobutyl)-1H-benzotriazole (0.06 mol) was dissolved into 150 ml of acetonitrile, 4-(3-(3-trifluoromethylphenyl) piperidine (0.05 mol), diisopropylethylamine (0.2 mol) and potassium iodide (0.05 mol) were respectively added. The mixture was stirred for 10 min at ambient temperature, and 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, purified, eluted with dichloromethane/methanol mixture to produce 13.5 g N-(4-(1H-benzotriazole-1-yl)butyl)-4-(3-trifluoromethylphenyl)piperidine (I-130) with a yield of 64.1%. ESI-MS [M+H]+: m/z 421.2.

Workup

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

Sources & evidence

ORD record
ord-a1742b8abc92406ab3b0b66274678283
Source dataset
uspto-grants-2016_08
Patent number
US09415047B2

Reaction notes

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