Réaction #11574

Équation de réaction

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

potassium carbonate

sodium iodide

2-chloroethyl methyl ether

→

titled compound

Rendement 32.1%

1-[2-(1-Adamantyl)ethyl]-1-[2-[N-(2-methoxyethyl)-N-methylamino]ethyl]-3-[3-(4-pyridyl)propyl]urea

Rendement 32.1%

Solvants

water

diethyl ether

N,N-dimethylformamide

Conditions de réaction

Traitement

1. 1
   Extractionthe whole was extracted
2. 2
   LavageThe obtained organic layer was washed with water (100 ml)
3. 3
   Séchagea saturated aqueous sodium chloride solution (50 ml), dried over anhydrous magnesium sulfate
4. 4
   Concentrationconcentrated under reduced pressure
5. 5
   AutreThe residue was purified by silica gel column chromatography

Mode opératoire

To N,N-dimethylformamide (20 ml) were added 1-[2-(1-adamantyl)ethyl]-1-(2-methylaminoethyl)-3-[3-(4-pyridyl)propyl]urea (1.50 g, 3.76 mmol), which was a free base of Compound No. 3-1, potassium carbonate (1.56 g, 11.3 mmol) and sodium iodide (1.69 g, 11.3 mmol) at room temperature, then 2-chloroethyl methyl ether (412 μl, 4.51 mmol) was added to the mixture, and the whole was heated at 80° C. The whole was stirred overnight, diethyl ether (50 ml) and water (100 ml) were added to the reaction mixture, and the whole was extracted. The obtained organic layer was washed with water (100 ml) and a saturated aqueous sodium chloride solution (50 ml), dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to give 552 mg (32.1%) of the titled compound as a pale yellow oily matter.

Source