Piperidine → 3,5-Dichloro-4-piperidin-1-ylmethylphenol

Participants

Reaction Steps

To a pre-stirred solution of 2,6-dichloro-4-hydroxybenzaldehyde (1.88, 9.8 mmol) and piperidine (1.07 mL, 10.8 mmol) in DCM (40 mL) was added sodium triacetoxyborohydride (3.13 g, 14.8 mmol) in portions. After 14 h the reaction mixture was quenched by the addition of water (50 mL), the pH of the solution adjusted to 2 by the addition of hydrochloric acid and the solution washed with DCM (50 mL). The pH of the aqueous phase was then adjusted to 9 by the addition of saturated aqueous sodium carbonate and then the organic component was extracted with DCM (50 mL), dried over anhydrous sodium sulfate and evaporated under reduced pressure to afford the title compound as a beige solid (2.03 g, 80%) that was used without further purification. 1H NMR (CD3OD, 300 MHz): 6.81-6.77 (m, 2H), 3.72 (s, 2H), 2.67-2.57 (m, 4H), 1.64-1.54 (m, 4H), 1.51-1.44 (m, 2H).

Provenance & Evidence