Reaction #1480363

Reaction equation

m-Chloroperbenzoic acid

1-[2-(1-adamantyl)ethyl]-1-pentyl-3-[3-(4-pyridyl)propyl]urea

sodium hydroxide

→

titled compound

Yield 94.2%

4-[3-[3-[2-(1-Adamantyl)ethyl]-3-pentylureido]propyl]pyridine N-oxide

Yield 94.2%

Solvents

chloroform

Conditions

Workup

1. 1
   WashThe organic layer was washed with water (10 ml)
2. 2
   Dryinga saturated aqueous sodium chloride solution (10 ml) successively and dried over anhydrous magnesium sulfate
3. 3
   OtherThe solvent was evaporated under reduced pressure
4. 4
   Otherthe resulting residue was purified by silica gel column chromatography

Procedure

m-Chloroperbenzoic acid (2.5 g, 15 mmol) was added to a solution of 1-[2-(1-adamantyl)ethyl]-1-pentyl-3-[3-(4-pyridyl)propyl]urea (Compound No. 1-1) (3.0 g, 7.3 mmol) at room temperature under a nitrogen atmosphere, and the mixture was stirred overnight. The reaction mixture was distributed with chloroform (20 ml) and a 1 N aqueous sodium hydroxide solution (60 ml). The organic layer was washed with water (10 ml) and a saturated aqueous sodium chloride solution (10 ml) successively and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the resulting residue was purified by silica gel column chromatography to give 2.92 g (94.2%) of the titled compound.

Source