Dimethylformamide → HCID 19878329, compound

Participants

Reaction Steps

Five g of the compound of Example 1 was combined with 10.9 g of potassium carbonate, 50 ml of dimethylformamide, and 2.9 g of 1-(2-chloroethyl)piperdine hydrochloride. The mixture was stirred under reflux for 1 hour under nitrogen, and it was then cooled and poured into 1500 ml of iced brine. The aqueous mixture was extracted 3 times with 200 ml portions of ethyl acetate, and the organic extract was washed 3 times with 25 ml portions of brine, dried and evaporated under vacuum to obtain 6.6 g of tan crystals. The impure product was purified by high performance liquid chromatography over silica gel, using 2% triethylamine and diethyl ether. The product-containing fractions were concentrated under vacuum to obtain 5.43 g of white crystals, which were recrystallized from 60 ml of acetone to obtain 3.95 g of pure product, m.p. 147°-148° C.

Provenance & Evidence