Potassium Carbonate → HCID 19911450, compound

Participants

Reaction Steps

A solution of 56.3 g (0.315 mol) of bis(2-chloroethyl)amine hydrochloride and 35.9 g (0.287 mol) of 4-fluoro-3-methylbenzeneamine in 500 mL of absolute ethanol was heated at reflux for 24 h under a nitrogen atmosphere. The mixture was cooled and 65.3 g (0.473 mol) of anhydrous potassium carbonate was added and heating was continued for 24 h. The hot mixture was filtered and the filtrate was concentrated under reduced pressure. The residue was triturated with ethyl acetate to yield a crude solid. This solid was converted to the base and purified by column chromatography using 500 g of silica gel on a 30 cm×10 cm column, eluted with methanol. The fractions containing the product were combined and concentrated. The residue was partitioned between water and ethyl ether. The ethyl ether layer was washed with water, dried (MgSO4) and concentrated under reduced pressure to yield 9.3 g (14%) of a light-pink oil. A portion of the oil was converted to the dihydrochloric acid salt and the solid was recrystallized from 2-propanol to yield a white solid, mp 188°-191° C.

Provenance & Evidence