Hydrogen Peroxide → HCID 57097142, compound

HRID 482277Notes

Reaction equation

HRID 482277 reaction equation
[CH2:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][N:12]2[CH2:17][CH2:16][CH:15]([C:18]([C:30]3[CH:35]=[CH:34][C:33]([C:36]([F:39])([F:38])[F:37])=[CH:32][CH:31]=3)([C:20]3[CH:25]=[CH:24][C:23]([C:26]([F:29])([F:28])[F:27])=[CH:22][CH:21]=3)[OH:19])[CH2:14][CH2:13]2)=[CH:7][CH:6]=1)[CH2:2][CH3:3].[OH:40]O.[Cl-].[Na+]>CO>[CH2:1]([O:4][C:5]1[CH:6]=[CH:7][C:8]([CH2:11][N+:12]2([O-:40])[CH2:13][CH2:14][CH:15]([C:18]([C:30]3[CH:31]=[CH:32][C:33]([C:36]([F:39])([F:37])[F:38])=[CH:34][CH:35]=3)([C:20]3[CH:25]=[CH:24][C:23]([C:26]([F:27])([F:28])[F:29])=[CH:22][CH:21]=3)[OH:19])[CH2:16][CH2:17]2)=[CH:9][CH:10]=1)[CH2:2][CH3:3]

Participants

5

Reactant 3

HCID 784Hydrogen Peroxide2×HCID 5234Sodium ChlorideHCID 22006953HCID 22006953, compound

Product 1

HCID 57097142HCID 57097142, compoundYield 88.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of 1.5 grams (0.003 mole) of N-(4-propoxyphenylmethyl)-4-[bis(4-trifluoromethylphenyl)hydroxymethyl]piperidine in 25.0 mL of absolute methanol was added 1.4 mL (0.014 mole) of 30% aqueous hydrogen peroxide in one portion. Upon completion of the addition the reaction mixture was stirred at ambient temperature for five hours and then analyzed by thin layer chromatography (TLC), which indicated the reaction was not complete. An additional 3.0 mL (0.029 mole) of 30% aqueous hydrogen peroxide was added, and the reaction mixture was stirred for about 18 hours. At the conclusion of this period the reaction mixture was poured into 100 mL of an aqueous saturated sodium chloride solution. The mixture was extracted with three 100 mL portions of ethyl acetate, and the combined extracts were washed with one 100 mL portion of an aqueous saturated sodium chloride solution. The organic layer was dried with sodium sulfate and filtered. The filtrate was concentrated under reduced pressure, yielding 1.5 grams of N-(4-propoxyphenylmethyl)-4-[bis(4-trifluoromethylphenyl)hydroxymethyl]piperidine N-oxide. The NMR spectrum was consistent with the proposed structure.

Workup

  1. additionUpon completion of the addition the reaction mixture
  2. stirringthe reaction mixture was stirred for about 18 hours
  3. extractionThe mixture was extracted with three 100 mL portions of ethyl acetate
  4. washthe combined extracts were washed with one 100 mL portion of an aqueous saturated sodium chloride solution
  5. dry with materialThe organic layer was dried with sodium sulfate
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-2868163eb23a4067be1911ddbccf44f1
Source dataset
uspto-grants-1998_08
Patent number
US05795901

Reaction notes

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