Dichloromethane → Tert-butyl 4-[(3,4-dichlorophenyl)sulfonyl]piperidine-1-carboxylate

HRID 1060811Notes

Reaction equation

HRID 1060811 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11](SC2C=CC(Cl)=C(Cl)C=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Cl:23][C:24]1[CH:29]=[CH:28][CH:27]=[C:26](C(OO)=O)[CH:25]=1.[S:34](S([O-])=O)([O-:37])(=O)=[O:35].[Na+].[Na+].[Cl:43]CCl>O>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([S:34]([C:26]2[CH:27]=[CH:28][C:29]([Cl:43])=[C:24]([Cl:23])[CH:25]=2)(=[O:37])=[O:35])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 70297m-Chloroperbenzoic acidHCID 656671Sodium PyrosulfiteHCID 685523534-(3,4-Dichloro-phenylsulfanyl)-piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 68550800Tert-butyl 4-[(3,4-dichlorophenyl)sulfonyl]piperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The product from Step 1(1 g) and m-chloroperbenzoic acid (1.19 g) were stirred at ambient temperature in dichloromethane (10 ml) for 18 hours. Sodium metabisulphite (1.19 g) in water (5 ml) was added and stirring was continued for 0.5 hours after which the reaction mixture was extracted with dichloromethane. The combined organics were washed with saturated sodium bicarbonate solution, dried (MgSO4) and evaporated to give the sub-title compound (0.34 g).

Workup

  1. extractionafter which the reaction mixture was extracted with dichloromethane
  2. washThe combined organics were washed with saturated sodium bicarbonate solution
  3. dry with materialdried (MgSO4)
  4. customevaporated

Sources & evidence

ORD record
ord-55d7ae52da294ccb8295770136173be4
Source dataset
uspto-grants-2003_02
Patent number
US06525070B2

Reaction notes

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