Potassium Iodide → 6-fluoro-3-(4-(4-(1H-benzotriazole-1-yl)butyl)piperazine-1-yl)benzisoxazole

HRID 1482594Notes

Reaction equation

HRID 1482594 reaction equation
Cl[CH2:2][CH2:3][CH2:4][CH2:5][N:6]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[N:8]=[N:7]1.[F:15][C:16]1[CH:30]=[CH:29][C:19]2[C:20]([N:23]3[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]3)=[N:21][O:22][C:18]=2[CH:17]=1.C(N(C(C)C)CC)(C)C.[I-].[K+]>C(#N)C>[F:15][C:16]1[CH:30]=[CH:29][C:19]2[C:20]([N:23]3[CH2:28][CH2:27][N:26]([CH2:2][CH2:3][CH2:4][CH2:5][N:6]4[C:10]5[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=5[N:8]=[N:7]4)[CH2:25][CH2:24]3)=[N:21][O:22][C:18]=2[CH:17]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 81531DiisopropylethylamineHCID 34251071-(4-chlorobutyl)-1H-benzotriazoleHCID 19805377HCID 19805377, compound

Product 1

HCID 762833906-fluoro-3-(4-(4-(1H-benzotriazole-1-yl)butyl)piperazine-1-yl)benzisoxazoleYield 70.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1-(4-chlorobutyl)-1H-benzotriazole (7.55 g, 0.036 mol) was dissolved into 100 ml of acetonitrile, 6-fluoro-3-(piperazine-1-yl)benzisoxazole (6.1 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 8.3 g compound (I-36) with a yield of 70.0%. ESI-MS [M+H]+: m/z 395.2.

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-9b47e6ac1c664d5ea9dea957ade6efe8
Source dataset
uspto-grants-2016_08
Patent number
US09415047B2

Reaction notes

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