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

Temperature

75 °C

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 to distribute it. The diethyl ether layer was washed with water (70 ml) twice and a saturated aqueous sodium chloride solution (120 ml) once successively, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. Then the obtained concentrate was purified by silica gel column chromatography to give the target compound (0.6 g, 40%) as an oily matter.

1. washThe diethyl ether layer was washed with water (70 ml) twice
2. dry with materiala saturated aqueous sodium chloride solution (120 ml) once successively, dried over anhydrous magnesium sulfate
3. concentrationconcentrated under reduced pressure
4. concentrationThen the obtained concentrate
5. customwas purified by silica gel column chromatography

ORD record

ord-b3013360acf7497db699e1a1d3e6ad1d

Source dataset

uspto-grants-2010_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07741346B2