Sodium Iodide → 5-[4-[4-(4-Fluorobenzoyl)piperidino]butyl]-2-methyl-2,3,4,5-tetrahydropyrrolo[2,3-e][1,2]thiazin-4-one 1,1-dioxide

HRID 1370722Notes

Reaction equation

HRID 1370722 reaction equation
Cl[CH2:2][CH2:3][CH2:4][CH2:5][N:6]1[C:10]2[C:11](=[O:18])[CH2:12][N:13]([CH3:17])[S:14](=[O:16])(=[O:15])[C:9]=2[CH:8]=[CH:7]1.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][CH2:5][N:6]3[C:10]4[C:11](=[O:18])[CH2:12][N:13]([CH3:17])[S:14](=[O:16])(=[O:15])[C:9]=4[CH:8]=[CH:7]3)[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 227149655-(4-Chlorobutyl)-2-methyl-2,3,4,5-tetrahydropyrrolo[2,3-e][1,2]thiazin-4-one 1,1-dioxide

Product 1

HCID 98043455-[4-[4-(4-Fluorobenzoyl)piperidino]butyl]-2-methyl-2,3,4,5-tetrahydropyrrolo[2,3-e][1,2]thiazin-4-one 1,1-dioxideYield 95.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A suspension of 145 mg (0.5 mmol) of Compound 17, 134 mg (0.55 mmol) of 4-(4-fluorobenzoyl)piperidine hydrochloride, 185 mg (2.2 mmol) of sodium hydrogencarbonate and 165 mg (1.1 mmol) of sodium iodide in 20 me of acetonitrile was refluxed for 50 hours. Posttreatment was conducted in a similar manner as in Example 18. The residue was purified by chromatography on a silica gel column (eluent: methanol/chloroform=3/97), whereby 220 mg of the title compound were obtained (yield: 95%).

Workup

  1. temperaturewas refluxed for 50 hours
  2. customThe residue was purified by chromatography on a silica gel column (eluent: methanol/chloroform=3/97)

Sources & evidence

ORD record
ord-a17bc063c6504498b28173d76e7ed5cc
Source dataset
uspto-grants-2003_06
Patent number
US06583296B2

Reaction notes

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