m-Chloroperbenzoic acid → 1-Methyl-4-phenoxy-4-phenylpiperidine N-oxide

HRID 1156037Notes

Reaction equation

HRID 1156037 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][C:5]([O:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:4][CH2:3]1.ClC1C=CC=C(C(OO)=[O:29])C=1>CO>[CH3:1][N+:2]1([O-:29])[CH2:7][CH2:6][C:5]([O:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:4][CH2:3]1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 3060394Piperidine, 1-methyl-4-phenoxy-4-phenyl-

Product 1

HCID 538883291-Methyl-4-phenoxy-4-phenylpiperidine N-oxide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

1.5 g of 1-methyl-4-phenoxy-4-phenylpiperidine are dissolved in 4 ml of methanol, and 1.7 g of 80% strength m-chloroperbenzoic acid, dissolved in methanol, are added slowly thereto while cooling with ice. After stirring the mixture at room temperature for 3 hours, the solvent is stripped off and the residue is partitioned between concentrated sodium hydroxide solution and chloroform. The crude N-oxide hydrate (which remains after drying the chloroform phase and evaporating off the solvent) is taken up in a little methanol, and the equivalent amount of methanolic fumaric acid is added. 1 g of a colorless precipitate is obtained.

Workup

  1. additionare added slowly
  2. temperaturewhile cooling with ice
  3. customthe residue is partitioned between concentrated sodium hydroxide solution and chloroform
  4. dry with materialafter drying the chloroform phase
  5. customevaporating off the solvent)
  6. additionthe equivalent amount of methanolic fumaric acid is added

Sources & evidence

ORD record
ord-73c031d5a4e942119bc30554cd4ce55d
Source dataset
uspto-grants-1982_06
Patent number
US04333942

Reaction notes

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