Sodium Iodide → HCID 23368052, compound

HRID 1901444Notes

Reaction equation

HRID 1901444 reaction equation
Cl[CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:15]=[N:14][C:13]2[CH2:12][CH2:11][CH2:10][CH2:9][C:8]=2[N:7]=1.C(=O)([O-])[O-].[K+].[K+].[N:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[N:28]1[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]1.[I-].[Na+]>C(#N)C>[N:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[N:28]1[CH2:29][CH2:30][N:31]([CH2:2][CH2:3][CH2:4][O:5][C:6]2[CH:15]=[N:14][C:13]3[CH2:12][CH2:11][CH2:10][CH2:9][C:8]=3[N:7]=2)[CH2:32][CH2:33]1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 944591-(2-Pyridyl)piperazineHCID 23368058HCID 23368058, compound

Product 1

HCID 23368052HCID 23368052, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

227 mg (1 mmol) of 2-(3-chloropropoxy)-5,6,7,8-tetrahydroquinoxaline was dissolved in 10 ml of acetonitrile. To the resultant solution were added 208 mg (1.5 mmol) of potassium carbonate, 196 mg (1.2 mmol) of 1-(2-pyridyl)piperazine and 149 mg (1 mmol) of sodium iodide, and the resultant mixture was heated under reflux for 15 hours. Then, the mixture was subjected to filtration to filter off insoluble substances, which were then washed with acetonitrile, to thereby obtain a filtrate. The solvent of the filtrate was distilled off in vacuo to thereby obtain a residue. The obtained residue was purified by silica gel column chromatography. That is, the residue was charged in a column of 20 g of silica gel (Art7734, manufactured and sold by E. Merck, Darmstadt) and eluted with chloroform-methanol (100:1), to thereby obtain 279 mg of 2-[3-{4-(2-pyridyl)-1-piperazinyl}propoxy]-5,6,7,8-tetrahydroquinoxaline (yield: 79%).

Workup

  1. temperatureunder reflux for 15 hours
  2. filtrationThen, the mixture was subjected to filtration
  3. filtrationto filter off insoluble substances, which
  4. washwere then washed with acetonitrile
  5. customto thereby obtain a filtrate
  6. distillationThe solvent of the filtrate was distilled off in vacuo
  7. customto thereby obtain a residue
  8. customThe obtained residue was purified by silica gel column chromatography
  9. additionthe residue was charged in a column of 20 g of silica gel (Art7734, manufactured and sold by E. Merck, Darmstadt)
  10. washeluted with chloroform-methanol (100:1)

Sources & evidence

ORD record
ord-55f230d3c27d400dae09670a891b20e5
Source dataset
uspto-grants-1996_11
Patent number
US05578596

Reaction notes

Loading…