Potassium Iodide → HCID 178490257, compound

HRID 1482625Notes

Reaction equation

HRID 1482625 reaction equation
ClCCC[N:5]1[C:9]2[CH:10]=[C:11]([O:14][CH3:15])[CH:12]=[CH:13][C:8]=2[N:7]=[N:6]1.[O:16]1[C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=2[C:18]([CH:25]2[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]2)=[N:17]1.[CH:31](N(C(C)C)CC)([CH3:33])[CH3:32].[I-].[K+]>C(#N)C>[O:14]([C:11]1[CH:12]=[C:13]([CH2:32][CH2:31][CH2:33][N:28]2[CH2:29][CH2:30][CH:25]([C:18]3[C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=4[O:16][N:17]=3)[CH2:26][CH2:27]2)[C:8]2[N:7]=[N:6][NH:5][C:9]=2[CH:10]=1)[CH3:15]

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 81531DiisopropylethylamineHCID 130764363-(Piperidin-4-yl)benzo[d]isoxazoleHCID 118386874N-(3-chloropropyl)-6-methoxyl benzotriazole

Product 1

HCID 178490257HCID 178490257, compoundYield 67.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

N-(3-chloropropyl)-6-methoxyl benzotriazole (0.06 mol) was dissolved into 150 ml of acetonitrile, 4-(3-benzisoxazolyl) 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 13.14 g N-(3-(6-methoxyl benzotriazolyl)propyl)-4-(3-benzisoxazolyl)piperidine (I-93) with a yield of 67.2%. ESI-MS [M+H]+: m/z 391.2.

Workup

  1. additionwere respectively added
  2. temperatureheated
  3. temperaturerefluxed
  4. customto react for 15 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. custompurified
  11. washeluted with dichloromethane/methanol mixture

Sources & evidence

ORD record
ord-0fa27cfb0b464c9e9025725321d459ae
Source dataset
uspto-grants-2016_08
Patent number
US09415047B2

Reaction notes

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