Reaktion #11576

Reaktionsgleichung

2-bromoacetic acid N-[2-(1-adamantyl)ethyl]-N-pentylamide

potassium carbonate

methyl iodide

4-(2-aminoethyl)pyridine

→

titled compound

Ausbeute 41.6%

2-[2-(4-Pyridyl)ethylamino]acetic acid N-[2-(1-adamantyl)ethyl]-N-pentylamide

Ausbeute 41.6%

Lösungsmittel

diethyl ether

Water

N,N-dimethylformamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   Waschenthe diethyl ether layer was washed with water (70 ml) twice
2. 2
   Trocknena saturated aqueous sodium chloride solution (120 ml) once successively and dried over anhydrous magnesium sulfate
3. 3
   EinengenThe diethyl ether layer was concentrated under reduced pressure
4. 4
   Sonstigethe concentrate was purified by silica gel column chromatography

Vorschrift

Next, 2-bromoacetic acid N-[2-(1-adamantyl)ethyl]-N-pentylamide (1.3 g, 3.5 mmol) was dissolved in anhydrous N,N-dimethylformamide (30 ml), potassium carbonate (1.5 g, 11 mmol), methyl iodide (1.6 g, 11 mmol) and 4-(2-aminoethyl)pyridine (0.43 g, 3.5 mmol) were added to the solution, and the mixture was stirred at an external temperature of 75° C. overnight. Water (100 ml) and diethyl ether (100 ml) were added to the reaction mixture, the reaction mixture was distributed, and the diethyl ether layer was washed with water (70 ml) twice and a saturated aqueous sodium chloride solution (120 ml) once successively and dried over anhydrous magnesium sulfate. The diethyl ether layer was concentrated under reduced pressure, and the concentrate was purified by silica gel column chromatography to give 0.6 g (40%) of the titled compound as an oily matter.

Quelle