Synthesis of 4-methoxy-N-{2-[3-(methylamino)phenyl}benzamide, and antiarrhythmic compound related to encainide

Article abstract of DOI:10.1055/s-1994-25615

A ring-opened side product 3, formed during the reduction of a pyridinium precursor to the antiarrhythmic drug, encainide (2), was isolated. The structure of 3 was confirmed by an independent synthesis from o-iodonitrobenzene and 1-hepten-3-ol. The key step was a palladium(II) catalyzed coupling to introduce the 3-oxoheptyl side chain onto the aromatic ring. Synthetic 3 exhibited significant antiarrhythmic activity.