Sodium Iodide → HCID 73863352, compound

HRID 1168606Notes

Reaction equation

HRID 1168606 reaction equation
Cl[CH2:2][CH2:3][CH2:4][N:5]1[CH2:11][CH2:10][C:9](=[N:12][OH:13])[C:8]2[N:14]([CH3:17])[CH:15]=[CH:16][C:7]=2[S:6]1(=[O:19])=[O:18].[F:20][C:21]1[CH:26]=[CH:25][C:24]([N:27]2[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]2)=[CH:23][CH:22]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>C(#N)C>[F:20][C:21]1[CH:22]=[CH:23][C:24]([N:27]2[CH2:32][CH2:31][N:30]([CH2:2][CH2:3][CH2:4][N:5]3[CH2:11][CH2:10][C:9](=[N:12][OH:13])[C:8]4[N:14]([CH3:17])[CH:15]=[CH:16][C:7]=4[S:6]3(=[O:19])=[O:18])[CH2:29][CH2:28]2)=[CH:25][CH:26]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 752601-(4-Fluorophenyl)piperazineHCID 73863353HCID 73863353, compound

Product 1

HCID 73863352HCID 73863352, compoundYield 29.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A suspension of 112 mg (0.4 mmol) of Compound 20, 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 18 hours. The reaction mixture was concentrated under reduced pressure, and a half-saturated aqueous solution of potassium carbonate was added to the residue. The water layer was saturated with sodium chloride, and the thus-obtained mixture was extracted with THF. The organic layer was 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 53 mg of the title compound were obtained (yield: 29%).

Workup

  1. temperaturewas refluxed for 18 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 thus-obtained mixture was extracted with THF
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by chromatography on a silica gel column (eluent: methanol/chloroform=3/97)

Sources & evidence

ORD record
ord-430d347fb8b2432b8f4741d5571d0dd1
Source dataset
uspto-grants-2003_09
Patent number
US06624314B2

Reaction notes

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