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

HRID 1293530Notes

Reaction equation

HRID 1293530 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-0b558e0d228a407ab3c3412cc73bb6f7
Source dataset
uspto-grants-2007_07
Patent number
US07238811B2

Reaction notes

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