Water → N-{2-[4-(4-Fluorobenzoyl)piperidino]ethyl}-4-(N-hydroxyimino)-N-(2-methoxyphenyl)benzenesulfonamide

HRID 2472

Reaction equation

HRID 2472 reaction equation
[F:1][C:2]1[CH:37]=[CH:36][C:5]([C:6]([CH:8]2[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][N:16]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=3[O:34][CH3:35])[S:17]([C:20]3[CH:25]=[CH:24][C:23](C=O)=[CH:22][CH:21]=3)(=[O:19])=[O:18])[CH2:10][CH2:9]2)=[O:7])=[CH:4][CH:3]=1.Cl.[OH:39][NH2:40].C(=O)([O-])[O-].[Na+].[Na+].O>C(O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([CH:8]2[CH2:9][CH2:10][N:11]([CH2:14][CH2:15][N:16]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=3[O:34][CH3:35])[S:17]([C:20]3[CH:21]=[CH:22][C:23](=[N:40][OH:39])[CH2:24][CH:25]=3)(=[O:19])=[O:18])[CH2:12][CH2:13]2)=[O:7])=[CH:36][CH:37]=1

Participants

6

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 443297Hydroxyamine hydrochlorideHCID 19689832N-{2-[4-(4-Fluorobenzoyl)piperidino]ethyl}-4-formyl-N-(2-methoxyphenyl)benzenesulfonamide

Product 1

HCID 86752291N-{2-[4-(4-Fluorobenzoyl)piperidino]ethyl}-4-(N-hydroxyimino)-N-(2-methoxyphenyl)benzenesulfonamideYield 102.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

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.

Workup

  1. customethanol was removed by evaporation
  2. additionthe resulting residue was mixed with water (10 ml)
  3. customto collect crystals
  4. filtrationby filtration
  5. washThe thus collected crystals were washed with water and hexane
  6. dissolutiondissolved in methylene chloride (50 ml)
  7. dry with materialdried on anhydrous sodium carbonate
  8. customThereafter, the solvent was removed by evaporation

Sources & evidence

ORD record
ord-4df58d28e9e34965aa240b18daf00714
Source dataset
uspto-grants-1998_03
Patent number
US05728835

Linked notes

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