Nitroxyl → N-[4-[2-(dibutylamino)-1-hydroxyethyl]phenyl]methanesulfonamide

HRID 466369

Reaction equation

HRID 466369 reaction equation
O=N.[CH2:3]([N:7]([CH2:22][CH2:23][CH2:24][CH3:25])[CH2:8][C:9]([C:11]1[CH:16]=[CH:15][C:14]([NH:17][S:18]([CH3:21])(=[O:20])=[O:19])=[CH:13][CH:12]=1)=[O:10])[CH2:4][CH2:5][CH3:6]>[Pd].CCO>[CH2:22]([N:7]([CH2:3][CH2:4][CH2:5][CH3:6])[CH2:8][CH:9]([C:11]1[CH:12]=[CH:13][C:14]([NH:17][S:18]([CH3:21])(=[O:20])=[O:19])=[CH:15][CH:16]=1)[OH:10])[CH2:23][CH2:24][CH3:25]

Participants

5

Reactant 2

HCID 945NitroxylHCID 19873466N-[4-[2-(Dibutylamino)-1-oxoethyl]phenyl]methanesulfonamide

Product 1

HCID 19873459N-[4-[2-(dibutylamino)-1-hydroxyethyl]phenyl]methanesulfonamide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 0.46 g (1.35 mmol) of the ketoamine free base, N-[4-[2-(Dibutylamino)-1-oxoethyl]phenyl]methanesulfonamide, 0.15 g of 10% palladium on carbon catalyst and 150 ml of absolute EtOH is placed on a Parr hydrogenator and shaken under an hydrogen atmosphere for 18.5 hrs. The catalyst is removed by filtration and the filtrate is concentrated in vacuo. The residue is chromatographed on a 100 ml silica gel column (elution with 3% MeOH:CH2Cl2 containing 0.3% NH4OH) and fractions are collected. The title compound is recrystallized from Et2O:pet. ether.

Workup

  1. customThe catalyst is removed by filtration
  2. concentrationthe filtrate is concentrated in vacuo
  3. customThe residue is chromatographed on a 100 ml silica gel column (elution with 3% MeOH:CH2Cl2 containing 0.3% NH4OH) and fractions
  4. customare collected
  5. customThe title compound is recrystallized from Et2O

Sources & evidence

ORD record
ord-515880a395ab4aaf96785221c93ee8f6
Source dataset
uspto-grants-1992_10
Patent number
US05155268

Linked notes

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