Potassium Iodide → HCID 178490258, compound

HRID 1482628Notes

Reaction equation

HRID 1482628 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.[S: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[S: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 133240934-(3-Benzisothiazolyl) piperidineHCID 118386874N-(3-chloropropyl)-6-methoxyl benzotriazole

Product 1

HCID 178490258HCID 178490258, compoundYield 69.1%

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-benzisothiazolyl) 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 13.17 g N-(3-(6-methoxyl benzotriazolyl)propyl)-4-(3-benzisothiazolyl)piperidine (I-100) with a yield of 69.1%. ESI-MS [M+H]+: m/z 426.2.

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-20856a6f014c4955a84593f4d5c89921
Source dataset
uspto-grants-2016_08
Patent number
US09415047B2

Reaction notes

Loading…