Hydrochloric Acid → 2-(3-(Piperidin-4-ylidenemethyl)phenoxy)-5-(trifluoromethyl)pyridine hydrochloride

Participants

Reaction Steps

4-[3-(5-Trifluoromethyl-pyridin-2-yloxy)-benzylidene]-piperidine-1-carboxylic acid tert-butyl ester (1.35 g, 3.11 mmol) from Step 4 was dissolved in CH2Cl2 (30 mL) and treated with HCl in diethyl ether (10 mL, 2.0 M, 20 mmol). After 16 hours the reaction was concentrated in vacuo to form a residue and the residue was suspended in acetonitrile (10 mL) to yield a solid. Filtration of the solid provided the title compound as a white solid (1.1 g). 1H NMR (400 MHz, CD3OD) δ ppm 2.62 (td, J=6.11, 0.91 Hz, 2H) 2.67-2.81 (m, 2H) 3.14-3.21 (m, 2H) 3.22-3.29 (m, 2H) 6.56 (s, 1H) 6.99-7.09 (m, 2H) 7.10-7.18 (m, 2H) 7.42 (t, J=7.91 Hz, 1H) 8.09 (ddd, J=8.74, 2.60, 0.33 Hz, 1H) 8.41 (td, J=1.63, 0.74 Hz, 1H).

Provenance & Evidence