m-Chloroperbenzoic acid → HCID 54183316, compound

HRID 634863Notes

Reaction equation

HRID 634863 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-ac37d1b1d2594e79b18bfa960762c2b4
Source dataset
uspto-grants-2001_02
Patent number
US06184234B2

Reaction notes

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