Sodium Iodide → HCID 9868923, compound

HRID 1168601Notes

Reaction equation

HRID 1168601 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].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[CH2:11][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])[CH2:29][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 22065888HCID 22065888, compound

Product 1

HCID 9868923HCID 9868923, compoundYield 74.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A suspension of 116 mg (0.4 mmol) of Compound 18, 97 mg (0.4 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 5 ml of acetonitrile was refluxed for 17 hours. Post treatment was conducted as in Example 13, and the residue was purified by chromatography on a silica gel column (eluent: methanol/chloroform=3/97), whereby 137 mg of the title compound were obtained (yield: 74%).

Workup

  1. temperaturewas refluxed for 17 hours
  2. customthe residue was purified by chromatography on a silica gel column (eluent: methanol/chloroform=3/97)

Sources & evidence

ORD record
ord-ae6dc351f7ca40b4ab9080faf5aa713b
Source dataset
uspto-grants-2003_09
Patent number
US06624314B2

Reaction notes

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