Reacción #2568

ord-4df58d28e9e34965aa240b18daf00714

Ecuación de reacción

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
Rendimiento 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
Rendimiento 102.7%

Disolventes

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    Otroethanol was removed by evaporation
  2. 2
    workup.ADDITIONthe resulting residue was mixed with water (10 ml)
  3. 3
    Otroto collect crystals
  4. 4
    Filtraciónby filtration
  5. 5
    LavadoThe thus collected crystals were washed with water and hexane
  6. 6
    workup.DISSOLUTIONdissolved in methylene chloride (50 ml)
  7. 7
    Secadodried on anhydrous sodium carbonate
  8. 8
    OtroThereafter, the solvent was removed by evaporation

Procedimiento

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.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US05728835uspto-grants-1998_03