Triethylamine → N-(6-Methylpyridin-2-yl)pivalamide

Participants

Reaction Steps

A 3-L flask equipped with a nitrogen (N2) inlet, thermometer and addition funnel was charged with dichloromethane (CH2Cl2, 1400 mL) and 2-amino-6-methylpyridine (130 g, 1.2 mol, Aldrich). After cooling the reaction to 0° C. in a wet ice/water bath, triethylamine (Et3N, 151.5 g, 1.5 mol) was added. Trimethylacetyl chloride (159.15 g, 1.32 mol) was diluted with CH2Cl2 (100 mL) and added dropwise to the reaction over 1.5 h. The reaction was stirred for an additional 30 min at room temperature. The salts were filtered from the reaction and the filtrate was washed twice with H2O. Drying the filtrate with anhydrous magnesium sulfate (MgSO4) and stripping all solvent in vacuo left a yellowish colored solid. Recrystallization from diethyl ether (Et2O)/hexanes (Hex) provided 167.3 g (73%) of pure product. The identity of this material and that of subsequent examples were confirmed by NMR (300 MHZ), microanalysis, and infrared spectroscopy, unless otherwise noted.

Provenance & Evidence