Reaktion #2568

ord-4df58d28e9e34965aa240b18daf00714

Reaktionsgleichung

O
water
COc1ccccc1N(CCN1CCC(C(=O)c2ccc(F)cc2)CC1)S(=O)(=O)c1ccc(C=O)cc1
N-{2-[4-(4-Fluorobenzoyl)piperidino]ethyl}-4-formyl-N-(2-methoxyphenyl)benzenesulfonamide
Cl.NO
hydroxyamine hydrochloride
O=C([O-])[O-].[Na+].[Na+]
sodium carbonate
COc1ccccc1N(CCN1CCC(C(=O)c2ccc(F)cc2)CC1)S(=O)(=O)C1=CCC(=NO)C=C1
title compound
Ausbeute 102.7%
COc1ccccc1N(CCN1CCC(C(=O)c2ccc(F)cc2)CC1)S(=O)(=O)C1=CCC(=NO)C=C1
N-{2-[4-(4-Fluorobenzoyl)piperidino]ethyl}-4-(N-hydroxyimino)-N-(2-methoxyphenyl)benzenesulfonamide
Ausbeute 102.7%

Lösungsmittel

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Sonstigeethanol was removed by evaporation
  2. 2
    workup.ADDITIONthe resulting residue was mixed with water (10 ml)
  3. 3
    Sonstigeto collect crystals
  4. 4
    Filtrationby filtration
  5. 5
    WaschenThe thus collected crystals were washed with water and hexane
  6. 6
    workup.DISSOLUTIONdissolved in methylene chloride (50 ml)
  7. 7
    Trocknendried on anhydrous sodium carbonate
  8. 8
    SonstigeThereafter, the solvent was removed by evaporation

Vorschrift

N-{2-[4-(4-Fluorobenzoyl)piperidino]ethyl}-4-formyl-N-(2-methoxyphenyl)benzenesulfonamide (63 mg, 0.12 mmol) and hydroxyamine hydrochloride (9.5 mg, 0.132 mmol) were dissolved in ethanol (2 ml) to which were subsequently added anhydrous sodium carbonate (14 mg, 0.132 mmol) and water (1 ml). After 1.5 hours of stirring at room temperature, ethanol was removed by evaporation, and the resulting residue was mixed with water (10 ml) to collect crystals by filtration. The thus collected crystals were washed with water and hexane, dissolved in methylene chloride (50 ml) and then dried on anhydrous sodium carbonate. Thereafter, the solvent was removed by evaporation to obtain 65 mg (100%) of the title compound in the form of colorless powder.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US05728835uspto-grants-1998_03