Reaktion #11578

Reaktionsgleichung

(R)-2-pyrrolidinecarboxylic acid N-[2-(1-adamantyl)ethyl]-N-pentylamide hydrochloride

sodium hydroxide

potassium carbonate

methyl iodide

4-(2-chloroethyl)pyridine hydrochloride

→

titled compound

Ausbeute 47.0%

(R)-1-[2-(4-Pyridyl)ethyl]-2-pyrrolidinecarboxylic acid N-[2-(1-adamantyl)ethyl]-N-pentylamide hydrochloride

Ausbeute 47.0%

Lösungsmittel

N,N-dimethylformamide

diethyl ether

Reaktionsbedingungen

Aufarbeitung

1. 1
   Waschenthe diethyl ether layer was washed with water (70 ml)
2. 2
   Trocknena saturated aqueous sodium chloride solution (70 ml) 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, (R)-2-pyrrolidinecarboxylic acid N-[2-(1-adamantyl)ethyl]-N-pentylamide hydrochloride (1.4 g, 3.7 mmol) was dissolved in anhydrous N,N-dimethylformamide (40 ml), potassium carbonate (2.6 g, 19 mmol), methyl iodide (1.7 g, 11 mmol) and 4-(2-chloroethyl)pyridine hydrochloride (0.70 g, 3.7 mmol) were added to the solution, and the mixture was stirred at an external temperature of 80° C. overnight. A 2 N aqueous sodium hydroxide solution (70 ml) and diethyl ether (70 ml) were added to the reaction mixture, the reaction mixture was distributed, and the diethyl ether layer was washed with water (70 ml) and a saturated aqueous sodium chloride solution (70 ml) 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 0.80 g (47%) of the titled compound as an oily matter.

Quelle