Trifluoroacetic acid → 2-Chloro-5-(piperidin-4-yloxy)pyridine

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Reaction Steps

A solution of 4-(6-chloro-pyridin-3-yloxy)-piperidine-1-carboxylic acid tert-butyl ester (5.68 g, 18.16 mmol) in DCM (2 mL) was treated with TFA (25 mL) and stirred at room temperature for 1 hour. The mixture was concentrated under vacuum, dissolved in 1 N aqueous HCl and washed with EtOAc. The aqueous a phase was basified with ammonium hydroxide and extracted into EtOAc. The combined extracts were dried over Na2SO4 and concentrated under vacuum to give 2-chloro-5-(piperidin-4-yloxy)-pyridine (4.58 g) as a yellow solid. 1H NMR (300 MHz, DMSO) δ 8.54 (br s, 1H), 8.18 (d, J=3.1 Hz, 1H), 7.60-7.53 (m, 1H), 7.45 (d, J=8.8 Hz, 1H), 4.76-4.65 (m, 1H), 3.30-3.19 (m, 2H), 3.11-3.00 (m, 2H), 2.15-2.03 (m, 2H), 1.89-1.74 (m, 2H). LCMS (m/z, Method A) ES+ 213.1 [M+1]+.

Provenance & Evidence