Reaktion #11581

Reaktionsgleichung

chloroform

hydrochloric acid

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

sodium hydroxide

→

titled compound

Ausbeute 21.7%

1-[2-(1-Adamantyl)ethyl]-1-(2-aminoethyl)-3-[3-(4-pyridyl)propyl]urea

Ausbeute 21.7%

Lösungsmittel

water

methanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturUnder ice-cooling
2. 2
   workup.ADDITIONwere added
3. 3
   Sonstigelayers were separated
4. 4
   WaschenThe organic layer was washed with a saturated aqueous sodium chloride solution (50 ml)
5. 5
   Trocknendried over anhydrous magnesium sulfate
6. 6
   Sonstigethe solvent was evaporated under reduced pressure
7. 7
   SonstigeThe residue was purified by silica gel column chromatography

Vorschrift

Under ice-cooling, 6 N hydrochloric acid (15 ml) was added to a solution of 1-[2-(acetylamino)ethyl]-1-[2-(1-adamantyl)ethyl]-3-[3-(4-pyridyl)propyl]urea (Compound No. 1-103) (1.02 g, 2.39 mmol) in methanol (10 ml), and the mixture was heated at 90° C. with stirring for three days. The reaction mixture was neutralized with a 1 N aqueous sodium hydroxide solution (10 ml), chloroform (50 ml) and water (10 ml) were added thereto, and layers were separated. The organic layer was washed with a saturated aqueous sodium chloride solution (50 ml) and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography to give 200 mg (21.7%) of the titled compound as an oily matter.

Quelle