Isopropanol → (2s,3r)-n-(2-((3-Pyridinyl)methyl)-1-azabicyclo[2.2.2]oct-3-yl)benzofuran-2-carboxamide maleate salt

Participants

Reaction Steps

Maleic acid (0.067 g, 0.630 mmol) was added to a hot slurry of (2S,3R)—N-(2-((3-pyridinyl)methyl)-1-azabicyclo[2.2.2]oct-3-yl)benzofuran-2-carboxamide (0.203 g, 0.560 mmol) in isopropyl acetate (2 mL), depositing fine, white solids, along with a gummy residue. Additional isopropyl acetate (3 mL) and maleic acid (0.006 g) were added, and the mixture was heated to reflux. Isopropanol (5 mL) was added at reflux. The resulting mixture of white solids was cooled to ambient temperature, filtered, and the solids were washed with isopropyl acetate (2 mL). The product was dried under vacuum at 60° C. for 18 h to give 0.228 g of an off-white, flaky solid (84.7% yield), mp 180-182° C. 1H NMR (DMSO-d6) indicated a mono-salt stoichiometry. Calc'd for C22H23N3O2.C4H4O4: C, 65.40; H, 5.70; N, 8.80; Found: C, 65.35, 65.29; H, 5.86, 5.68; N, 8.69, 8.78.

Provenance & Evidence