m-Chloroperbenzoic acid → HCID 54000351, compound

HRID 866062Notes

Reaction equation

HRID 866062 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:31]3[CH:36]=[CH:35][C:34]([O:37][C:38]([F:41])([F:40])[F:39])=[CH:33][CH:32]=3)([C:20]3[CH:25]=[CH:24][C:23]([O:26][C:27]([F:30])([F:29])[F:28])=[CH:22][CH:21]=3)[OH:19])[CH2:14][CH2:13]2)=[CH:7][CH:6]=1)[CH:2]=[CH2:3].ClC1C=C(C=CC=1)C(OO)=[O:47]>C(Cl)(Cl)Cl>[CH2:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][N+:12]2([O-:47])[CH2:13][CH2:14][CH:15]([C:18]([C:20]3[CH:25]=[CH:24][C:23]([O:26][C:27]([F:28])([F:29])[F:30])=[CH:22][CH:21]=3)([C:31]3[CH:32]=[CH:33][C:34]([O:37][C:38]([F:41])([F:39])[F:40])=[CH:35][CH:36]=3)[OH:19])[CH2:16][CH2:17]2)=[CH:7][CH:6]=1)[CH:2]=[CH2:3]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 19040917HCID 19040917, compound2×

Product 1

HCID 54000351HCID 54000351, compoundYield 41.8%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a stirred solution of 0.5 gram (0.0008 mole) of N-[4-(2-propen-1-yloxy)phenylmethyl]-4-[bis(4-trifluoromethoxyphenyl)hydroxymethyl]piperidine (Compound 42, prepared in Example 5) in 10 mL of chloroform was added 0.3 gram (0.0008 mole) of 50% 3-chloroperoxybenzoic acid. Upon completion of addition, the reaction mixture was stirred at ambient temperature for about 2 hours. After this time the reaction mixture was washed, first, with an aqueous solution saturated with sodium bicarbonate, and then with an aqueous solution saturated with sodium chloride. The organic layer was dried with magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure to a residue, which was subjected to column chromatography on silica gel, with mixtures of ethyl acetate and hexane as eluants. The product-containing fractions were combined and concentrated under reduced pressure to a residue. The residue was concentrated further under high vacuum, yielding about 0.2 gram of N-[4-(2-propen-1-yloxy)phenylmethyl]-4-[bis(4-trifluoromethoxyphenyl)hydroxymethyl]piperidine N-oxide. The NMR spectrum was consistent with the proposed structure.

Workup

  1. additionUpon completion of addition
  2. washAfter this time the reaction mixture was washed
  3. dry with materialThe organic layer was dried with magnesium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated under reduced pressure to a residue, which
  6. concentrationconcentrated under reduced pressure to a residue
  7. concentrationThe residue was concentrated further under high vacuum

Sources & evidence

ORD record
ord-4188f1b079d842d4bf48d53c60a1f64a
Source dataset
uspto-grants-1996_10
Patent number
US05569664

Reaction notes

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