m-Chloroperbenzoic acid → HCID 19030940, compound

HRID 1648579Notes

Reaction equation

HRID 1648579 reaction equation
[CH2:1]([O:6][C:7]1[CH:31]=[CH:30][C:10]([C:11]([N:13]2[CH2:18][CH2:17][CH:16]([N:19]3[C:29]4[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=4)[CH2:23][CH2:22][C:20]3=[O:21])[CH2:15][CH2:14]2)=[O:12])=[CH:9][CH:8]=1)[CH2:2][CH2:3][CH:4]=[CH2:5].ClC1C=CC=C(C(OO)=[O:40])C=1.C(=O)([O-])O.[Na+]>ClCCl>[O:40]1[CH2:5][CH:4]1[CH2:3][CH2:2][CH2:1][O:6][C:7]1[CH:31]=[CH:30][C:10]([C:11]([N:13]2[CH2:18][CH2:17][CH:16]([N:19]3[C:29]4[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=4)[CH2:23][CH2:22][C:20]3=[O:21])[CH2:15][CH2:14]2)=[O:12])=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 19030775HCID 19030775, compound

Product 1

HCID 19030940HCID 19030940, compoundYield 72.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-{1-[4-(4-Pentenyloxy)benzoyl]-4-piperidinyl}-3,4-dihydrocarbostyril (2 g) is dissolved in dichloromethane (50 ml) and thereto is added gradually m-chloroperbenzoic acid (1.6 g) at room temperature. The mixture is stirred under the same conditions overnight and the reaction mixture is poured into aqueous sodium hydrogen carbonate solution and the mixture is extracted with chloroform and dried with magnesium sulfate. The solvent is distilled off and the resulting residue is purified by silica gel column chromatography (solvent: n-hexane:ethyl acetate=1:1) to give 1-{1-[4-(3-oxiranylpropoxy)benzoyl]-4-piperidinyl}-3,4-dihydrocarbostyril (1.5 g).

Workup

  1. extractionthe mixture is extracted with chloroform
  2. dry with materialdried with magnesium sulfate
  3. distillationThe solvent is distilled off
  4. customthe resulting residue is purified by silica gel column chromatography (solvent: n-hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-b373dd3e27de42889ac4be4fa8972ad2
Source dataset
uspto-grants-1995_07
Patent number
US05436254

Reaction notes

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