Piperidine → 1-(3-Bromo-5-methoxybenzyl)piperidine

To a pre-stirred solution of 3-bromo-5-methoxybenzaldehyde (0.56 g, 2.61 mmol) and piperidine (0.29 mL, 3.93 mmol) in DCM (10 mL) at 0° C. was added sodium borohydride (197 mg, 5.22 mmol) in portions. The reaction mixture was allowed to warm to ambient temperature and stirred for an additional 2 h. The reaction was quenched by the addition of water (30 mL) and extracted into ethyl acetate (75 mL) then washed with water (50 mL) then the organic phase was dried over anhydrous sodium sulfate, filtered and evaporated in vacuo to afford the title compound as a colourless oil (510 mg, 69%) that was used in the next step without further purification. 1H NMR (CDCl3, 400 MHz): 7.08-7.06 (m, 1H), 6.94-6.91 (m, 1H), 6.83-6.80 (s, 1H), 3.79 (s, 3H), 3.39 (s, 2H), 2.40-2.30 (s, 4H), 1.61-1.51 (m, 4H), 1.47-1.38 (m, 2H).

1. customThe reaction was quenched by the addition of water (30 mL)
2. extractionextracted into ethyl acetate (75 mL)
3. washthen washed with water (50 mL)
4. dry with materialthe organic phase was dried over anhydrous sodium sulfate
5. filtrationfiltered
6. customevaporated in vacuo

ORD record

ord-68c4936ffead43dbbc91c291c5dee62b

Source dataset

uspto-grants-2013_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08501765B2