m-Chloroperbenzoic acid → HCID 14053216, compound

HRID 1252505Notes

Reaction equation

HRID 1252505 reaction equation
[CH3:1][C:2]1[C:3]([N:19]2[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]2)=[CH:4][C:5]([CH2:8][S:9][C:10]2[NH:11][C:12]3[C:17]([CH:18]=2)=[CH:16][CH:15]=[CH:14][CH:13]=3)=[N:6][CH:7]=1.ClC1C=CC=C(C(OO)=[O:33])C=1>C(Cl)(Cl)Cl>[CH3:1][C:2]1[C:3]([N:19]2[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]2)=[CH:4][C:5]([CH2:8][S:9]([C:10]2[NH:11][C:12]3[C:17]([CH:18]=2)=[CH:16][CH:15]=[CH:14][CH:13]=3)=[O:33])=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 14053215HCID 14053215, compound

Product 1

HCID 14053216HCID 14053216, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To a solution of 2-[(5-methyl-4-piperidino-2-pyridyl)methylthio]indole (80 mg, 0.24 mmol) in chloroform (2.4 ml) was added m-chloroperbenzoic acid (60 mg, 0.35 mmol) under ice-cooling, and the mixture was stirred at that temperature for further 30 minutes. The reaction solution was diluted with chloroform (10 ml) and then washed with a 1% aqueous sodium hydrogen carbonate solution (2.5 ml) and then with a saturated aqueous sodium chloride solution (1 ml). The resulting chloroform layer was dried over anhydrous magnesium sulfate and then concentrated in vacuo. Ethylether (20 ml) was added to the resulting concentration residue to precipitate crystals. After filtration, the titled compound (68 mg) was obtained. Yield: 81%, m.p.: 178° C.

Workup

  1. temperaturecooling
  2. washwashed with a 1% aqueous sodium hydrogen carbonate solution (2.5 ml)
  3. dry with materialThe resulting chloroform layer was dried over anhydrous magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. additionEthylether (20 ml) was added to the resulting concentration residue
  6. customto precipitate crystals
  7. filtrationAfter filtration

Sources & evidence

ORD record
ord-08c1b7ce3bb24f0da881de0f70089a3a
Source dataset
uspto-grants-1988_05
Patent number
US04743609

Reaction notes

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