Sodium Iodide → HCID 85051146, compound

HRID 1828246Notes

Reaction equation

HRID 1828246 reaction equation
Cl[CH2:2][CH2:3][CH2:4][N:5]1[CH2:10][C:9](=[N:11][OH:12])[C:8]2[N:13]([CH3:16])[CH:14]=[CH:15][C:7]=2[S:6]1(=[O:18])=[O:17].Cl.[F:20][C:21]1[CH:34]=[CH:33][C:24]([C:25]([CH:27]2[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]2)=[O:26])=[CH:23][CH:22]=1.C(=O)([O-])O.[Na+].[I-].[Na+]>C(#N)C>[F:20][C:21]1[CH:22]=[CH:23][C:24]([C:25]([CH:27]2[CH2:32][CH2:31][N:30]([CH2:2][CH2:3][CH2:4][N:5]3[CH2:10][C:9](=[N:11][OH:12])[C:8]4[N:13]([CH3:16])[CH:14]=[CH:15][C:7]=4[S:6]3(=[O:18])=[O:17])[CH2:29][CH2:28]2)=[O:26])=[CH:33][CH:34]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 516892Sodium BicarbonateHCID 3084438p-Fluorophenyl 4-piperidyl ketone hydrochlorideHCID 73863356HCID 73863356, compound

Product 1

HCID 85051146HCID 85051146, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A suspension of 116 mg (0.4 mmol) of Compound 19, 389 mg (0.6 mmol) of 4-(4-fluorobenzoyl)piperidine hydrochloride, 134 mg (1.6 mmol) of sodium hydrogencarbonate and 120 mg (0.8 mmol) of sodium iodide in 8 ml of acetonitrile was refluxed for 24 hours. The reaction mixture was filtered, and the filtrate was concentrated under reduced pressure. The residue was purified by chromatography on a silica gel column (eluent: methanol/methylene chloride=1/15), whereby 90 mg of the title compound were obtained (yield: 49%).

Workup

  1. temperaturewas refluxed for 24 hours
  2. filtrationThe reaction mixture was filtered
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe residue was purified by chromatography on a silica gel column (eluent: methanol/methylene chloride=1/15)

Sources & evidence

ORD record
ord-918ec362c7324956917e05f40a217b6e
Source dataset
uspto-grants-2006_06
Patent number
US07057036B2

Reaction notes

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