m-Chloroperbenzoic acid → HCID 14576906, compound

HRID 1904625Notes

Reaction equation

HRID 1904625 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:13]([C:14]3[CH:19]=[CH:18][C:17]([S:20]([CH3:22])=[O:21])=[CH:16][CH:15]=3)[CH2:12][CH2:11][CH2:10][C:9]2=[O:23])=[CH:4][CH:3]=1.ClC1C=CC=C(C(OO)=[O:32])C=1.C(=O)([O-])O.[Na+]>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:13]([C:14]3[CH:19]=[CH:18][C:17]([S:20]([CH3:22])(=[O:32])=[O:21])=[CH:16][CH:15]=3)[CH2:12][CH2:11][CH2:10][C:9]2=[O:23])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 14576905HCID 14576905, compound

Product 1

HCID 14576906HCID 14576906, compoundYield 88.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1.70 g of 1-(4-chlorophenyl)-6-(4-methylsulfinylphenyl)-2-piperidone in 50 ml of methylene chloride was added 1.02 g of m-chloroperbenzoic acid with stirring at 5° to 10° C. over 30 minutes. After stirring at 5° to 10° C. for 1 hour and at room temperature for 1 hour, the mixture was made alkaline with a saturated aqueous sodium hydrogen carbonate solution. The methylene chloride layer was washed with water, dried, and concentrated. The residue was recrystallized from nitroethane to give 1.54 g of 1-(4-chlorophenyl)-6-(4-methylsulfonylphenyl)-2-piperidone as colorless prisms.

Workup

  1. stirringAfter stirring at 5° to 10° C. for 1 hour and at room temperature for 1 hour
  2. washThe methylene chloride layer was washed with water
  3. customdried
  4. concentrationconcentrated
  5. customThe residue was recrystallized from nitroethane

Sources & evidence

ORD record
ord-934fadccb5514516a7d6ed62fcb6b14a
Source dataset
uspto-grants-1989_06
Patent number
US04839360

Reaction notes

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