Trifluoroacetic acid → 6-(Morpholin-4-ylmethyl)pyridin-2-amine

Participants

Reaction Steps

To a solution of tert-butyl [6-(morpholin-4-ylmethyl)pyridin-2-yl]carbamate (114 mg, 0.39 mmol) in dichloromethane (3 mL) was added trifluoroacetic acid (1.2 mL, 16 mmol) at room temperature. After 3 hours, the reaction mixture was concentrated under reduced pressure, and saturated aqueous sodium carbonate was added to adjust to pH˜9. The mixture was extracted with ethyl acetate (3×), and the combined organic layers were dried over magnesium sulfate, filtered, and concentrated under reduced pressure to afford 6-(morpholin-4-ylmethyl)pyridin-2-amine that was used without further purification. MS ESI calc'd for C10H16N3O [M+H]+ 194. found 194. 1H NMR (500 MHz, DMSO-d6) δ 7.32 (t, J=7.7 Hz, 1H), 6.52 (d, J=7.2 Hz, 1H), 6.30 (d, J=8.2 Hz, 1H), 5.90 (s, 2H), 3.63-3.49 (m, 4H), 3.40-3.25 (m, 2H), 2.41 (s, 4H).

Provenance & Evidence