Sodium Iodide → HCID 9889134, compound

HRID 1828243Notes

Reaction equation

HRID 1828243 reaction equation
Cl[CH2:2][CH2:3][CH2:4][N:5]1[CH2:11][CH2:10][C:9](=[O:12])[C:8]2[N:13]([CH3:16])[CH:14]=[CH:15][C:7]=2[S:6]1(=[O:18])=[O:17].[F:19][C:20]1[CH:25]=[CH:24][C:23]([N:26]2[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]2)=[CH:22][CH:21]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>C(#N)C>[F:19][C:20]1[CH:21]=[CH:22][C:23]([N:26]2[CH2:31][CH2:30][N:29]([CH2:2][CH2:3][CH2:4][N:5]3[CH2:11][CH2:10][C:9](=[O:12])[C:8]4[N:13]([CH3:16])[CH:14]=[CH:15][C:7]=4[S:6]3(=[O:18])=[O:17])[CH2:28][CH2:27]2)=[CH:24][CH:25]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 752601-(4-Fluorophenyl)piperazineHCID 22065888HCID 22065888, compound

Product 1

HCID 9889134HCID 9889134, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A suspension of 116 mg (0.4 mmol) of Compound 18, 108 mg (0.6 mmol) of 1-(4-fluorophenyl)piperazine, 83 mg (0.6 mmol) of potassium carbonate and 120 mg (0.8 mmol) of sodium iodide in 6 ml of acetonitrile was refluxed for 19 hours. The reaction mixture was concentrated under reduced pressure, a half-saturated aqueous solution of potassium carbonate was added to the residue, and the resultant mixture was extracted with ethyl acetate. The organic layer was washed successively with water and a saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The residue was purified by chromatography on a silica gel column (eluent: methanol/chloroform=3/97), whereby 173 mg of the title compound were obtained (yield: 100%).

Workup

  1. temperaturewas refluxed for 19 hours
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. additiona half-saturated aqueous solution of potassium carbonate was added to the residue
  4. extractionthe resultant mixture was extracted with ethyl acetate
  5. washThe organic layer was washed successively with water
  6. dry with materiala saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by chromatography on a silica gel column (eluent: methanol/chloroform=3/97)

Sources & evidence

ORD record
ord-4b6b166d89a54934800ad82a211fc5ac
Source dataset
uspto-grants-2006_06
Patent number
US07057036B2

Reaction notes

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