Potassium Iodide → 1-(4-(4-cyclohexyl piperazine-1-yl)butyl)-1H-benzotriazole

HRID 1482604Notes

Reaction equation

HRID 1482604 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.[CH:15]1([N:21]2[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]2)[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1.C(N(C(C)C)CC)(C)C.[I-].[K+]>C(#N)C>[CH:15]1([N:21]2[CH2:26][CH2:25][N:24]([CH2:2][CH2:3][CH2:4][CH2:5][N:6]3[C:10]4[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=4[N:8]=[N:7]3)[CH2:23][CH2:22]2)[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 81531DiisopropylethylamineHCID 872981-CyclohexylpiperazineHCID 34251071-(4-chlorobutyl)-1H-benzotriazole

Product 1

HCID 762836391-(4-(4-cyclohexyl piperazine-1-yl)butyl)-1H-benzotriazoleYield 63.7%

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, 4-(1-cyclohexyl)piperazine (5.1 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 20 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 6.5 g compound (I-46) with a yield of 63.7%. ESI-MS [M+H]+: m/z 341.2.

Workup

  1. additionwere respectively added
  2. additionmixed
  3. temperatureheated
  4. temperaturerefluxed
  5. customto react for 20 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-17464e0ab7044a8aaddff41fc879f33a
Source dataset
uspto-grants-2016_08
Patent number
US09415047B2

Reaction notes

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