m-Chloroperbenzoic acid → 5-chloro-2-methyl-3-(piperidin-4-yl-sulfinyl)-1H-indole

HRID 36888Notes

Reaction equation

HRID 36888 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[Cl:12][C:13]1[CH:14]=[C:15]2[C:19](=[CH:20][CH:21]=1)[NH:18][C:17]([CH3:22])=[C:16]2[S:23][CH:24]1[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]1>ClCCl>[Cl:12][C:13]1[CH:14]=[C:15]2[C:19](=[CH:20][CH:21]=1)[NH:18][C:17]([CH3:22])=[C:16]2[S:23]([CH:24]1[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]1)=[O:9]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 152292715-chloro-2-methyl-3-(piperidin-4-ylthio)-1H-indole

Product 1

HCID 199366325-chloro-2-methyl-3-(piperidin-4-yl-sulfinyl)-1H-indole

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Metachloroperbenzoic acid (2.79 g) is added in portions to a solution of 5-chloro-2-methyl-3-(piperidin-4-ylthio)-1H-indole (3 g, prepared in Example 18) in dichloromethane (25 ml) at -40° C. After 4 hours at room temperature, the insoluble material is filtered off. The filtrate is washed with sodium hydroxide and then with water. The aqueous phases are extracted with ether and then with ethyl acetate. The organic phases are combined, dried over magnesium sulfate and concentrated. The oily residue obtained is chromatographed on silica gel (eluent: CH2Cl2 /MeOH/NH4OH:90/10/1) to give 5-chloro-2-methyl-3-(piperidin-4-yl-sulfinyl)-1H-indole in the form of an oil, which crystallizes on the addition of ether (0.4 g).

Workup

  1. filtrationthe insoluble material is filtered off
  2. washThe filtrate is washed with sodium hydroxide
  3. extractionThe aqueous phases are extracted with ether
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated
  6. customThe oily residue obtained
  7. customis chromatographed on silica gel (eluent: CH2Cl2 /MeOH/NH4OH:90/10/1)

Sources & evidence

ORD record
ord-a69a7a5567b54828bf7d98a8f58d346e
Source dataset
uspto-grants-1995_05
Patent number
US05418242

Reaction notes

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