Potassium Iodide → HCID 86587246, compound

HRID 1267624Notes

Reaction equation

HRID 1267624 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:13]2[CH:18]=[C:17]([CH2:19][N:20]3[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]3)[CH:16]=[CH:15][N:14]=2)[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9][CH3:10].CS(O[CH2:31][CH2:32][CH2:33][C:34]1[CH:39]=[C:38]([O:40][CH3:41])[C:37]([O:42][CH3:43])=[C:36]([O:44][CH3:45])[CH:35]=1)(=O)=[O:28].[I-].[K+].[C:48](=[O:51])([O-:50])[O-].[K+].[K+]>C(#N)C.O>[C:8]([OH:9])(=[O:28])/[CH:7]=[CH:6]\[C:48]([OH:50])=[O:51].[C:38]([OH:40])(=[O:2])/[CH:39]=[CH:34]\[C:48]([OH:50])=[O:51].[CH3:45][O:44][C:36]1[CH:35]=[C:34]([CH2:33][CH2:32][CH2:31][N:23]2[CH2:24][CH2:25][N:20]([CH2:19][C:17]3[CH:16]=[CH:15][N:14]=[C:13]([C:5]4[CH:6]=[C:7]([O:11][CH3:12])[C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=4)[CH:18]=3)[CH2:21][CH2:22]2)[CH:39]=[C:38]([O:40][CH3:41])[C:37]=1[O:42][CH3:43]

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 120211551-[[2-(3,4,5-Trimethoxyphenyl)pyridin-4-yl]-methyl]piperazineHCID 22931918HCID 22931918, compound

Product 1

HCID 86587246HCID 86587246, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
70 °C

Procedure

1-[[2-(3,4,5-Trimethoxyphenyl)pyridin-4-yl]-methyl]piperazine (57 mg) was dissolved in acetonitrile (4 mL), and to the solution 3-(3,4,5-trimethoxyphenyl)propyl methanesulfonate (50 mg), potassium iodide (35 mg) and potassium carbonate (46 mg) were added, and the mixture was stirred at 70° C. for 2 hours. Water was added to the reaction mixture to conduct extraction with chloroform. The resultant organic layer was washed with saturated brine, dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (chloroform:methanol=20:1). Maleic acid was added to the resultant oil to produce a salt, thereby obtaining the title compound.

Workup

  1. extractionextraction with chloroform
  2. washThe resultant organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by column chromatography on silica gel (chloroform:methanol=20:1)
  6. additionMaleic acid was added to the resultant oil
  7. customto produce a salt

Sources & evidence

ORD record
ord-5ff8aabde0a24a3c9764c90439ef5e96
Source dataset
uspto-grants-2003_04
Patent number
US06552188B2

Reaction notes

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