Sodium Hydroxide → HCID 13825047, compound

HRID 648500Notes

Reaction equation

HRID 648500 reaction equation
[Cl:1]C1C=CC=C(C(OO)=[O:9])C=1.Cl.[F:13][C: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.S(=O)(O)[O-].[Na+].[OH-].[Na+]>C(Cl)(Cl)Cl>[ClH:1].[F:13][C:14]1[CH:15]=[CH:16][C:17]([S:20]([CH:21]2[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]2)=[O:9])=[CH:18][CH:19]=1

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 70297m-Chloroperbenzoic acidHCID 136080004-[(4-Fluorophenyl)sulfanyl]piperidine--hydrogen chloride (1/1)HCID 23665763Sodium Bisulfite

Product 1

HCID 13825047HCID 13825047, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

3-Chloroperbenzoic acid (0.96 g) was slowly added to a stirred solution of 4-[(4-fluorophenyl)thio]piperidine hydrochloride (I.2g) in chloroform (60 ml) under ice-cooling over a period of 5 minutes and the mixture was stirred at the same temperature for 45 minutes. After being treated with sodium bisulfite solution under ice-cooling, the resultant mixture was adjusted to alkaline pH with 20% sodium hydroxide solution. The chloroform layer was separated and the aqueous layer was extracted three times with chloroform. The chloroform layers were combined and dried over magnesium sulfate. After removal of magnesium sulfate, the solution was treated with ethereal hydrochloric acid and concentrated to dryness in vacuo. The powdery residue was washed with isopropanol to give 4-[(4-fluorophenyl)sulfinyl]piperidine hydrochloride (1.10 g) as colourless powser.

Workup

  1. temperaturecooling over a period of 5 minutes
  2. temperaturecooling
  3. customThe chloroform layer was separated
  4. extractionthe aqueous layer was extracted three times with chloroform
  5. dry with materialdried over magnesium sulfate
  6. customAfter removal of magnesium sulfate
  7. additionthe solution was treated with ethereal hydrochloric acid
  8. concentrationconcentrated to dryness in vacuo
  9. washThe powdery residue was washed with isopropanol

Sources & evidence

ORD record
ord-a6c46c69459a4215934713eabf10bc2b
Source dataset
uspto-grants-1988_04
Patent number
US04735952

Reaction notes

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