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Synthesis 1994; 1994(9): 965-968
DOI: 10.1055/s-1994-25615
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Synthesis of 4-Methoxy-N-{2-[3-(Methylamino)heptyl]phenyl}benzamide, an Antiarrhythmic Compound Related to Encainide

Michael D. Thompson* , Houshang Torabi
  • *Chemical Process Development, Bristol-Myers Squibb, Co., Evansville, Indiana 47721, USA
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Publication Date:
17 September 2002 (online)

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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.