m-Chloroperbenzoic acid → HCID 54183316, compound

HRID 323830Notes

Reaction equation

HRID 323830 reaction equation
[CH3:1][N:2]1[N:6]=[N:5][C:4]([C:7]2[CH:12]=[CH:11][C:10]([CH2:13][N:14]3[CH2:19][CH2:18][CH:17]([C:20]([C:32]4[CH:37]=[CH:36][C:35]([C:38]([F:41])([F:40])[F:39])=[CH:34][CH:33]=4)([C:22]4[CH:27]=[CH:26][C:25]([C:28]([F:31])([F:30])[F:29])=[CH:24][CH:23]=4)[OH:21])[CH2:16][CH2:15]3)=[CH:9][CH:8]=2)=[N:3]1.ClC1C=C(C=CC=1)C(OO)=[O:47]>C(Cl)Cl>[CH3:1][N:2]1[N:6]=[N:5][C:4]([C:7]2[CH:8]=[CH:9][C:10]([CH2:13][N+:14]3([O-:47])[CH2:15][CH2:16][CH:17]([C:20]([C:22]4[CH:27]=[CH:26][C:25]([C:28]([F:29])([F:30])[F:31])=[CH:24][CH:23]=4)([C:32]4[CH:33]=[CH:34][C:35]([C:38]([F:41])([F:39])[F:40])=[CH:36][CH:37]=4)[OH:21])[CH2:18][CH2:19]3)=[CH:11][CH:12]=2)=[N:3]1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 22006951HCID 22006951, compound

Product 1

HCID 54183316HCID 54183316, compoundYield 84.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 1.1 grams (0.002 mole) of N-[4-(2-methyl-2H-tetrazol-5-yl)phenylmethyl]-4-[bis(4-trifluoromethylphenyl)hydroxymethyl]piperidine (Compound 31—prepared in Example 9) in 100 mL of methylene chloride was stirred, and 0.6 gram (excess) of 50-85% 3-chloroperoxybenzoic acid was added. Upon completion of addition, the reaction mixture was stirred at ambient temperature for about one hour. After this time the reaction mixture was washed with an aqueous 10% solution of sodium hydroxide. The organic layer was dried with magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, yielding 1.0 gram of N-[4-(2-methyl-2H-tetrazol-5-yl)phenyl-methyl]-4-[bis(4-trifluoromethylphenyl)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 with an aqueous 10% solution of sodium hydroxide
  3. dry with materialThe organic layer was dried with magnesium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-7d2946d13ed144f2b30e07d5d24f49b2
Source dataset
uspto-grants-2001_04
Patent number
US06214845B1

Reaction notes

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