Potassium Iodide → HCID 76282663, compound

HRID 1482582Notes

Reaction equation

HRID 1482582 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]=[CH: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]=[CH: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 583170Benzimidazole, 1-(4-chlorobutyl)-

Product 1

HCID 76282663HCID 76282663, compoundYield 62.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1-(4-chlorobutyl)-1H-benzimidazole (7.51 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 for 10 min at ambient temperature, and 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, eluted with dichloromethane/methanol mixture to produce 6.4 g compound (I-15) with a yield of 62.9%. ESI-MS [M+H]+: m/z 341.3.

Workup

  1. additionwere respectively added
  2. temperatureheated
  3. temperaturerefluxed
  4. customto react for 20 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-96e41236c6c946a889c28377b4c6a96c
Source dataset
uspto-grants-2016_08
Patent number
US09415047B2

Reaction notes

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