Hydrochloric Acid → 4-(4-Methylsulfonylaminophenylsulfinyl)-1-[2-(3-pyridyl)ethyl]piperidine

HRID 1090955Notes

Reaction equation

HRID 1090955 reaction equation
[CH3:1][S:2]([NH:5][C:6]1[CH:11]=[CH:10][C:9]([S:12][CH:13]2[CH2:18][CH2:17][N:16]([CH2:19][CH2:20][C:21]3[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=3)[CH2:15][CH2:14]2)=[CH:8][CH:7]=1)(=[O:4])=[O:3].I([O-])(=O)(=O)=[O:28].[Na+].Cl.[OH-].[Na+]>CO>[CH3:1][S:2]([NH:5][C:6]1[CH:11]=[CH:10][C:9]([S:12]([CH:13]2[CH2:14][CH2:15][N:16]([CH2:19][CH2:20][C:21]3[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=3)[CH2:17][CH2:18]2)=[O:28])=[CH:8][CH:7]=1)(=[O:4])=[O:3]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 156154214-(4-Methylsulfonylaminophenylthio)-1-[2-(3-pyridyl)ethyl]piperidineHCID 23667635Sodium periodate

Product 1

HCID 156154234-(4-Methylsulfonylaminophenylsulfinyl)-1-[2-(3-pyridyl)ethyl]piperidineYield 65.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 0.50 g (1.28 mmol) of 4-(4-methylsulfonylaminophenylthio)-1-[2-(3-pyridyl)-ethyl]piperidine, 0.33 g (1.53 mmol) of sodium periodate, 5 ml of 1 N hydrochloric acid and 5 ml of methanol was stirred at room temperature for 1 h. About 5 ml of a 1 N sodium hydroxide solution was added thereto to adjust the pH to about 7. After extraction with chloroform, the organic layer was concentrated and the residue was purified by silica gel column chromatography (CHCl3 :CH3OH: NH4OH=95:5:0.5). The fraction containing the intended compound was concentrated to give a solid residue, which was recrystallized from ethyl acetate to give a 0.34 g (yield: 64%) of the compound.

Workup

  1. extractionAfter extraction with chloroform
  2. concentrationthe organic layer was concentrated
  3. customthe residue was purified by silica gel column chromatography (CHCl3 :CH3OH: NH4OH=95:5:0.5)
  4. additionThe fraction containing the intended compound
  5. concentrationwas concentrated
  6. customto give a solid residue, which
  7. customwas recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-c66c7babeab94a37a482c82aca3676ee
Source dataset
uspto-grants-1992_01
Patent number
US05082850

Reaction notes

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