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

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).

1. customAfter 14 h the reaction mixture was quenched by the addition of water (50 mL)
2. additionthe pH of the solution adjusted to 2 by the addition of hydrochloric acid
3. washthe solution washed with DCM (50 mL)
4. additionThe pH of the aqueous phase was then adjusted to 9 by the addition of saturated aqueous sodium carbonate
5. extractionthe organic component was extracted with DCM (50 mL)
6. dry with materialdried over anhydrous sodium sulfate
7. customevaporated under reduced pressure

ORD record

ord-ffa7dd28daf44283baa3f03960ae0dc3

Source dataset

uspto-grants-2013_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08501765B2