Sodium Iodide → HCID 74953269, compound

HRID 1370727Notes

Reaction equation

HRID 1370727 reaction equation
Cl[CH2:2][CH2:3][CH2:4][CH2:5][N:6]1[C:10]2[C:11](=[N:19][OH:20])[CH2:12][CH2:13][N:14]([CH3:18])[S:15](=[O:17])(=[O:16])[C:9]=2[CH:8]=[CH:7]1.Cl.[F:22][C:23]1[CH:36]=[CH:35][C:26]([C:27]([CH:29]2[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]2)=[O:28])=[CH:25][CH:24]=1.C(=O)([O-])O.[Na+].[I-].[Na+]>C(#N)C>[F:22][C:23]1[CH:24]=[CH:25][C:26]([C:27]([CH:29]2[CH2:34][CH2:33][N:32]([CH2:2][CH2:3][CH2:4][CH2:5][N:6]3[C:10]4[C:11](=[N:19][OH:20])[CH2:12][CH2:13][N:14]([CH3:18])[S:15](=[O:17])(=[O:16])[C:9]=4[CH:8]=[CH:7]3)[CH2:31][CH2:30]2)=[O:28])=[CH:35][CH:36]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 516892Sodium BicarbonateHCID 3084438p-Fluorophenyl 4-piperidyl ketone hydrochlorideHCID 72612001HCID 72612001, compound

Product 1

HCID 74953269HCID 74953269, compoundYield 64.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A suspension of 110 mg (0.34 mmol) of Compound 21, 83 mg (0.34 mmol) of 4-(4-fluorobenzoyl)piperidine hydrochloride, 114 mg (1.36 mmol) of sodium hydrogen-carbonate and 102 mg (0.68 mmol) of sodium iodide in 10 ml of acetonitrile was refluxed for 17 hours. Post-treatment was conducted in a similar manner as in Example 18. The residue was purified by chromatography on a silica gel column (eluent: methanol/chloroform=11/189), whereby 108 mg of the title compound were obtained (yield: 64%).

Workup

  1. temperaturewas refluxed for 17 hours
  2. customThe residue was purified by chromatography on a silica gel column (eluent: methanol/chloroform=11/189)

Sources & evidence

ORD record
ord-346da859d2b24fb9af2254fc631f52bf
Source dataset
uspto-grants-2003_06
Patent number
US06583296B2

Reaction notes

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