m-Chloroperbenzoic acid → 4-[4-(4-(6-Chloronaphthalene-2-sulfonyl)piperazine-1-carbonyl)phenyl]pyridine 1-oxide

HRID 278607Notes

Reaction equation

HRID 278607 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([S:12]([N:15]1[CH2:20][CH2:19][N:18]([C:21](=[O:34])[C:22]3[CH:27]=[CH:26][C:25]([C:28]4[CH:33]=[CH:32][N:31]=[CH:30][CH:29]=4)=[CH:24][CH:23]=3)[CH2:17][CH2:16]1)(=[O:14])=[O:13])[CH:6]=[CH:5]2.ClC1C=CC=C(C(OO)=[O:43])C=1>ClCCl>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([S:12]([N:15]1[CH2:20][CH2:19][N:18]([C:21]([C:22]3[CH:23]=[CH:24][C:25]([C:28]4[CH:33]=[CH:32][N+:31]([O-:43])=[CH:30][CH:29]=4)=[CH:26][CH:27]=3)=[O:34])[CH2:17][CH2:16]1)(=[O:14])=[O:13])[CH:6]=[CH:5]2

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 99572891-[(6-Chloronaphthalen-2-yl)sulfonyl]-4-[4-(pyridin-4-yl)benzoyl]piperazine

Product 1

HCID 226280974-[4-(4-(6-Chloronaphthalene-2-sulfonyl)piperazine-1-carbonyl)phenyl]pyridine 1-oxideYield 91%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 1-(6-chloronaphthalene-2-sulfonyl)-4-[4-(4-pyridyl)benzoyl]piperazine (200 mg) in dichloromethane (25 ml) was added m-chloroperbenzoic acid (140 mg) and the solution was stirred at room temperature for 2 hours. The reaction solution was diluted with dichloromethane, washed with 1 N sodium hydroxide solution and sodium chloride solution, dried and concentrated. The residue was crystallized with dichloromethane/hexane to give a colorless solid of the title compound (188 mg).

Workup

  1. washwashed with 1 N sodium hydroxide solution and sodium chloride solution
  2. customdried
  3. concentrationconcentrated
  4. customThe residue was crystallized with dichloromethane/hexane

Sources & evidence

ORD record
ord-95c7f9a8ad8542728d65715d64b11988
Source dataset
uspto-grants-2002_03
Patent number
US06359134B1

Reaction notes

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