Hydrochloric Acid → 1-(2-Chloro-4,6-dimethoxybenzyl)-piperidine

To a pre-stirred solution of 2-chloro-4,6-dimethoxybenzaldehyde (2.7 g, 13.5 mmol) and piperidine (1.46 mL, 14.9 mmol) in DCM (50 mL) at 0° C. was added sodium triacetoxyborohydride (4.29 g, 20.0 mmol) in portions. The reaction mixture was then allowed to warm to ambient and stirred for an additional 3 h before the addition of water (50 mL). The pH of the aqueous phase was adjusted to 2 by the addition of hydrochloric acid and then 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 into DCM (50 mL), dried over sodium sulfate and evaporated under reduced pressure to afford the title compound as a beige solid (3.3 g, 91%) that was used without further purification. 1H NMR (CDCl3, 300 MHz): 6.60 (d, J=2.4 Hz, 1H), 6.43 (d, J=2.4 Hz, 1H), 4.35 (s, 2H), 3.90 (s, 3H), 3.83 (s, 3H), 3.6-2.57 (v br m, 4H), 2.29-1.88 (br m, 4H), 1.71-1.40 (br m, 2H).

1. temperatureto warm to ambient and
2. washwashed with DCM (50 mL)
3. additionThe pH of the aqueous phase was then adjusted to 9 by the addition of saturated aqueous sodium carbonate
4. extractionthe organic component was extracted into DCM (50 mL)
5. dry with materialdried over sodium sulfate
6. customevaporated under reduced pressure

ORD record

ord-166eda1ba2664304823db1c269dcfdb4

Source dataset

uspto-grants-2013_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08501765B2