Reacción #11574

Ecuación de reacción

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

potassium carbonate

sodium iodide

2-chloroethyl methyl ether

→

titled compound

Rendimiento 32.1%

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

Rendimiento 32.1%

Disolventes

water

diethyl ether

N,N-dimethylformamide

Condiciones de reacción

Tratamiento posterior

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

Procedimiento

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.

Fuente