Sodium Sulfite → 4-[4-(4-(6-Chloronaphthalene-2-sulfonyl)piperazine-1-carbonyl)phenyl]pyridine 1-oxide

HRID 1061059Notes

Reaction equation

HRID 1061059 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.S([O-])([O-])=O.[Na+].[Na+].C(=O)(O)[O-].[Na+]>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

6

Reactant 4

HCID 24437Sodium SulfiteHCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 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-oxide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-20 °C

Procedure

In dichloromethane (10 ml), 1-[(6-chloronaphthalen-2-yl)sulfonyl]-4-[4-(pyridin-4-yl)benzoyl]piperazine (300 mg) obtained in Example 1 was dissolved, followed by the addition of 3-chloroperbenzoic acid (382 g) at −20° C. The resulting mixture was stirred at −20° C. for 21 hours. An aqueous solution of sodium sulfite was added to decompose an excess peroxide. Dichloromethane and a saturated aqueous solution of sodium bicarbonate were added to separate an organic layer. After drying the organic layer over anhydrous magnesium sulfate, the residue obtained by distilling off the solvent was purified by chromatography on a silica gel column (2-5% methanol-dichloromethane). After the solvent was distilled off, ether was added to the residue to solidify it, followed by collection through filtration, whereby the title compound (200 mg, 63%) was obtained as a colorless solid.

Workup

  1. customto separate an organic layer
  2. dry with materialAfter drying the organic layer over anhydrous magnesium sulfate
  3. customthe residue obtained
  4. distillationby distilling off the solvent
  5. customwas purified by chromatography on a silica gel column (2-5% methanol-dichloromethane)
  6. distillationAfter the solvent was distilled off
  7. additionether was added to the residue
  8. filtrationfollowed by collection through filtration, whereby the title compound (200 mg, 63%)
  9. customwas obtained as a colorless solid

Sources & evidence

ORD record
ord-17fa707ffece4edc97be2c1e8b9ad943
Source dataset
uspto-grants-2003_02
Patent number
US06525042B1

Reaction notes

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