Zacopride → N-(1-Azabicyclo[2.2.2]oct-3-yl)-5-chloro-4-[[(dimethylamino)methylene]amino]-2-methoxybenzamide

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Reaction Steps

A solution of 4-amino-N-(1-azabicyclo[2.2.2]oct-3-yl)-5-chloro-2-methoxybenzamide (4.03 g, 13 mmol) in dimethylformamide dimethyl acetal (15 mL) and anhydrous dimethylformamide (5 mL) was heated to 100° C. for 4 hours, then concentrated in vacuo. The residue was dissolved in 6:1 tetrahydrofuran/methanol and filtered through a short column of alumina (eluted with 6:1 tetrahydrofuran/methanol). The filtrate was concentrated in vacuo to a purple residue, which was triturated from cold ether and recrystallized (2 crops) from acetonitrile to afford 2.88 g (61%) of fine colorless needles; mp 178.5°-179.5° C.

Provenance & Evidence