Sodium Perborate → 4-[(4-Chlorophenyl)sulfinyl]piperidine, Monohydrochloride

HRID 236096

Reaction equation

HRID 236096 reaction equation
O.Cl.[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([S:10][CH:11]2[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]2)=[CH:6][CH:5]=1.B(O[O-])=[O:18].[Na+]>Cl>[ClH:3].[Cl:3][C:4]1[CH:5]=[CH:6][C:7]([S:10]([CH:11]2[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]2)=[O:18])=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 517072Sodium PerborateHCID 202177794-[(p-Chlorophenyl)thio]piperidine hydrochloride hydrate

Product 1

HCID 855277194-[(4-Chlorophenyl)sulfinyl]piperidine, Monohydrochloride

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of 5.78 g (0.020 mole) of 4-[(p-chlorophenyl)thio]piperidine hydrochloride hydrate and 4.61 g (0.030 mole) of sodium perborate in 200 ml of dilute hydrochloride acid was stirred at room temperature overnight. The reaction mixture was quenched in dilute sodium hydroxide and the resulting basic solution was extracted with methylene chloride. The methylene chloride layer was dried over magnesium sulfate and the solvent was removed in vacuo to give a white solid, the free base of the title compound. The free base was reacted with ethereal hydrogen chloride and the salt was recrystallized from methanol-diethyl ether to give the product as a white crystalline solid, m.p. 22°-221° C.

Workup

  1. customThe reaction mixture was quenched in dilute sodium hydroxide
  2. extractionthe resulting basic solution was extracted with methylene chloride
  3. dry with materialThe methylene chloride layer was dried over magnesium sulfate
  4. customthe solvent was removed in vacuo
  5. customto give a white solid

Sources & evidence

ORD record
ord-41df8b20d978420eb4eb3a991d6c8d0b
Source dataset
uspto-grants-1987_02
Patent number
US04642348

Linked notes

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