Hydrochloric Acid → HCID 86706860, compound

Participants

Reaction Steps

4.0 M Hydrogen chloride in dioxane (12 mL, 47 mmol) was added to a solution of tert-butyl 4-{[4-(hydroxymethyl)-6-(trifluoromethyl)pyridin-2-yl]oxy}piperidine-1-carboxylate (0.89 g, 2.4 mmol, from Step 3) in 1,4-dioxane (12 mL) and the reaction was stirred for 3 hours. The reaction was made basic by the addition of 1N NaOH to achieve a pH between 12 and 13. The product was extracted with DCM (6×) and the combined extracts were dried over sodium sulfate, filtered and concentrated to afford product as a light yellow solid (0.50 g, 75%). 1H NMR (300 MHz, CDCl3) δ 7.22 (s, 1H), 6.91 (s, 1H), 5.23 (tt, J=7.9, 3.8 Hz, 1H), 4.74 (s, 2H), 3.26-3.06 (m, 2H), 2.88 (ddd, J=12.3, 8.6, 3.4 Hz, 2H), 2.11 (ddt, J=12.9, 6.7, 3.2 Hz, 2H), 1.92-1.56 (m, 2H). 19F NMR (282 MHz, CDCl3) δ −68.89 (s). LCMS (M+H)+: 277.0.

Provenance & Evidence