3-Chloro-N,N-dimethyl-1-propanamine → HCID 14837044, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 10 g of sodium bicarbonate, 4.0 g of 4-(2,3,4,5,6-pentafluorophenoxy)piperidine, and 50 ml of dimethylformamide was treated, dropwise, with a solution of 2.00 g of dimethylaminopropyl chloride in 20 ml of dimethylformamide. After stirring at 80° C. for eight hours, 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 solution of sodium chloride and dried over anhydrous magnesium sulfate. After filtering, evaporation of the volatiles afforded a residue which was eluted with 20% methanol/dichloromethane on a silica gel column via flash chromatography. The desired fractions were evaporated to afford 2.74 g of 1-[3-(N,N-dimethylamino)propyl]-4-(2,3,4,5,6-pentaflurophenoxy)piperidine as an oil. The oil was dissolved in isopropanol and acidified to pH 1 with etheral hydrogen chloride to precipitate 1.8 g (28%) of 1-[3-dimethylaminopropyl]-4-(2,3,4,5,6-pentaflurophenoxy)piperidine hydrochloride, m.p. 260° C.(dec.).

Provenance & Evidence