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

HRID 349745Notes

Reaction equation

HRID 349745 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-977f4554d94b4372bdddc62f30c3f896
Source dataset
uspto-grants-2007_02
Patent number
US07179922B2

Reaction notes

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