Sodium Hydroxide → 4-[3-[3-[2-(1-Adamantyl)ethyl]-3-pentylureido]propyl]pyridine N-oxide
Reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[C:12]12([CH2:22][CH2:23][N:24]([CH2:37][CH2:38][CH2:39][CH2:40][CH3:41])[C:25]([NH:27][CH2:28][CH2:29][CH2:30][C:31]3[CH:36]=[CH:35][N:34]=[CH:33][CH:32]=3)=[O:26])[CH2:21][CH:16]3[CH2:17][CH:18]([CH2:20][CH:14]([CH2:15]3)[CH2:13]1)[CH2:19]2.[OH-].[Na+]>C(Cl)(Cl)Cl>[C:12]12([CH2:22][CH2:23][N:24]([CH2:37][CH2:38][CH2:39][CH2:40][CH3:41])[C:25](=[O:26])[NH:27][CH2:28][CH2:29][CH2:30][C:31]3[CH:32]=[CH:33][N+:34]([O-:9])=[CH:35][CH:36]=3)[CH2:13][CH:14]3[CH2:15][CH:16]([CH2:17][CH:18]([CH2:20]3)[CH2:19]1)[CH2:21]2Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
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.
Workup
- washThe organic layer was washed with water (10 ml)
- dry with materiala saturated aqueous sodium chloride solution (10 ml) successively and dried over anhydrous magnesium sulfate
- customThe solvent was evaporated under reduced pressure
- customthe resulting residue was purified by silica gel column chromatography
Sources & evidence
- ORD record
- ord-61443c96d3b94ae2ba7d9e66418e3f1b
- Source dataset
- uspto-grants-2011_04
- Patent number
- US07923461B2
Reaction notes
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