Sodium Thiosulfate → HCID 22931018, compound

HRID 459860Notes

Reaction equation

HRID 459860 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[N:16]=[C:15]([C:17]([N:19]3[CH2:24][CH2:23][N:22]([C:25]4[CH:30]=[CH:29][N:28]=[CH:27][CH:26]=4)[CH2:21][CH2:20]3)=[O:18])[CH:14]=[CH:13][CH:12]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].ClC1C=CC=C(C(OO)=[O:39])C=1.S([O-])([O-])(=O)=S.[Na+].[Na+]>ClCCl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[N:16]=[C:15]([C:17]([N:19]3[CH2:20][CH2:21][N:22]([C:25]4[CH:26]=[CH:27][N+:28]([O-:39])=[CH:29][CH:30]=4)[CH2:23][CH2:24]3)=[O:18])[CH:14]=[CH:13][CH:12]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

5

Reactant 3

HCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acidHCID 22930983HCID 22930983, compound

Product 1

HCID 22931018HCID 22931018, compoundYield 80.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a dichloromethane (10 ml) solution of 353 mg of 1-[6-(3,4-dimethoxyphenyl)pyridine-2-carbonyl]-4-(pyridin-4-yl)piperazine was added 195 mg of m-chloroperbenzoic acid, followed by 1 hour of stirring at 50C. An aqueous sodium thiosulfate solution was added to the reaction solution, followed by extraction with chloroform. The organic layer was washed with water and brine and then dried over anhydrous magnesium sulfate, and thereafter, the solvent was evaporated. The residue was purified by silica gel column chromatography (chloroform-methanol) and then recrystallization (ethanol-ethyl acetate) was carried out to obtain 294 mg of 1-[6-(3,4-dimethoxyphenyl)pyridine-2-carbonyl]-4-(1-oxidopyridin-4-yl) piperazine 1.5 hydrate as pale yellow crystals.

Workup

  1. extractionfollowed by extraction with chloroform
  2. washThe organic layer was washed with water and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated
  5. customThe residue was purified by silica gel column chromatography (chloroform-methanol)
  6. customrecrystallization (ethanol-ethyl acetate)

Sources & evidence

ORD record
ord-593a3b60155e471997f08b1c8100a00c
Source dataset
uspto-grants-2007_03
Patent number
US07196080B2

Reaction notes

Loading…