2-Chloro-N,N-dimethylethylamine → HCID 14837042, compound

Participants

Reaction Conditions

Reaction Steps

A stirred mixture of 5 g of sodium bicarbonate, 4.44 g of 4-(2,3,4,5,6-pentafluorophenoxy)piperidine, and 40 ml of dimethylformamide was treated, dropwise, with a solution of 2.15 g of 2-dimethylaminoethyl chloride in 20 ml of dimethylformamide. After stirring for five hours at 85° C., the reaction mixture was filtered, and the filtrate poured into water and extracted with ethyl acetate. The organic layer was washed with water followed by a saturated sodium chloride solution and dried over anhydrous magnesium sulfate. After filtering, evaporation of the volatiles afforded an oil which was eluted with 20% methanol/dichloromethane on a silica gel column via flash chromatography. The desired fractions were evaporated to afford 2.58 g of 1-[2-(N,N-dimethylamino)ethyl]-4-(2,3,4,5,6-pentafluorophenoxy)piperidine as an oil. The oil was dissolved in isopropanol and the solution acidified to pH 1 with etheral hydrogen chloride to precipitate 2.05 g (29.3%) of the corresponding dihydrochloride salt, m.p. 276° C. (dec.).

Provenance & Evidence