Sodium Hydroxide → HCID 13825045, compound

HRID 648514Notes

Reaction equation

HRID 648514 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.Cl.Cl.[N:14]1[CH:19]=[CH:18][C:17]([S:20][CH:21]2[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]2)=[CH:16][CH:15]=1.[OH-].[Na+]>O>[N:14]1[CH:19]=[CH:18][C:17]([S:20]([CH:21]2[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]2)=[O:9])=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 70297m-Chloroperbenzoic acidHCID 219060714-[(Piperidin-4-yl)sulfanyl]pyridine--hydrogen chloride (1/2)

Product 1

HCID 13825045HCID 13825045, compoundYield 90.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

m-Chloroperbenzoic acid (1.20 g) was added to a stirred solution of 4-[(4-pyridyl)thio]piperidine dihydrochloride (1.33 g) in water (30 ml) under ice-cooling, and the mixture was stirred at the same temperature for 3 hours and then at room temperature for 5.5 hours. The resultant mixture was diluted with water and the pH of the mixture was adjusted to about 11 with 5% sodium hydroxide solution. The solution was extracted several times with chloroform. The extracts were combined, dried over magnesium sulfate, and concentrated in vacuo. The oily residue was crystallized from n-hexane and the crystals were recrystallized from a mixture of n-hexane and isopropanol to give 4-[(4-pyridyl)sulfinyl]piperidine (0.95 g).

Workup

  1. temperaturecooling
  2. waitat room temperature for 5.5 hours
  3. extractionThe solution was extracted several times with chloroform
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe oily residue was crystallized from n-hexane
  7. customthe crystals were recrystallized from a mixture of n-hexane and isopropanol

Sources & evidence

ORD record
ord-09af10bf57a74df392acd0c5cc89614d
Source dataset
uspto-grants-1988_04
Patent number
US04735952

Reaction notes

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