4-Hydroxybenzoic Acid → 3,5-Difluorobenzamide mono-4-hydroxybenzoate

Participants

Reaction Steps

To a solution of 71.5 mg (0.20 mmol) of (2S,3R)-N-2-((3-pyridinyl)methyl)-1-azabicyclo[2.2.2]oct-3-yl)-3,5-difluorobenzamide in 3.5 mL of isopropyl acetate was added 100 μL (0.1 mmol, 0.5 eq) of a 1M 4-hydroxylbenzoic acid in THF solution. The isopropyl acetate was evaporated to yield (2S,3R)-N-2-((3-pyridinyl)methyl)-1-azabicyclo[2.2.2]oct-3-yl)-3,5-difluorobenzamide mono-4-hydroxybenzoate as a solid which was collected and dried under vacuum at 25° C. for 24 h. mp(DSC)=106.0° C. 1H NMR (400 MHz, DMSO-d6) δ 10.23 (br s), 8.43 (s, 1H), 8.29 (s, 1H), 8.28 (s, 1H), 7.78 (d, 1H), 7.61 (m, 1H), 7.41 (m, 3H), 7.22 (m, 1H), 6.80 (d, 1H), 3.66 (m, 1H), 2.70-3.20 (m, 7H), 1.50-1.90 (m, 4H), 1.20 (m, 1H).

Provenance & Evidence