Sodium Hydroxide → HCID 13825050, compound

HRID 648505Notes

Reaction equation

HRID 648505 reaction equation
[Cl:1]C1C=CC=C(C(OO)=[O:9])C=1.Cl.Cl.[N:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[S:20][CH:21]1[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1.[OH-].[Na+]>O>[ClH:1].[N:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[S:20]([CH:21]1[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1)=[O:9]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 70297m-Chloroperbenzoic acid2×HCID 135640052-[(Piperidin-4-yl)sulfanyl]pyridine--hydrogen chloride (1/2)

Product 1

HCID 13825050HCID 13825050, compoundYield 75.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

m-Chloroperbenzoic acid (0.77 g) was added to an ice-cooled solution of 4-[(2-pyridyl)thio]piperidine dihydrochloride (1.0 g) in water (20 ml) and the mixture was stirred at the same temperature for 7.5 hours. After additional m-chloroperbenzoic acid (0.07 g) and water (5 ml) were added, the mixture was stirred at the same temperature for 1 hour, adjusted to alkaline pH with sodium hydroxide solution, and extracted several times with chloroform. The extracts were combined, dried over magnesium sulfate, and concentrated in vacuo. The oily residue was dissolved in chloroform. The solution was treated with ethanolic hydrochloric acid and concentrated in vacuo. The crystalline residue was washed with isopropanol to give 4-[(2-pyridyl)sulfinyl]piperidine hydrochloride (0.70 g).

Workup

  1. stirringthe mixture was stirred at the same temperature for 1 hour
  2. extractionextracted several times with chloroform
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. dissolutionThe oily residue was dissolved in chloroform
  6. additionThe solution was treated with ethanolic hydrochloric acid
  7. concentrationconcentrated in vacuo
  8. washThe crystalline residue was washed with isopropanol

Sources & evidence

ORD record
ord-55c1c39f86ce467c9e67ca66bdb40750
Source dataset
uspto-grants-1988_04
Patent number
US04735952

Reaction notes

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