Piperidine → 1-[(4-Bromo-2-chlorophenyl)methyl]piperidine

To a pre-stirred solution of 4-bromo-2-chlorobenzaldehyde (1.01 g, 4.6 mmol) and piperidine (500 μL, 5.0 mmol) in DCM (20 mL) at 0° C. was added sodium triacetoxyborohydride (1.46 g, 6.9 mmol) in portions. The reaction mixture was allowed to warm to ambient temperature and then partitioned between water (50 mL) and dichloromethane (50 mL). The organic phase was separated, washed with saturated aqueous sodium carbonate (50 mL), dried over anhydrous sodium sulfate, filtered and evaporated in vacuo. The resultant residue was loaded onto a 20 g SCX-2 cartridge which was washed with methanol then 2N ammonia in methanol. Concentration of the combined basic fractions in vacuo afforded the title compound as a colourless oil (1.15 g, 87%). 1H NMR (CDCl3, 400 MHz): 7.50-7.48 (m, 1H); 7.40-7.33 (m, 2H); 3.50 (s, 2H); 2.46-2.38 (m, 4H); 1.62-1.53 (m, 4H); 1.49-1.40 (m, 2H). LCMS (Method B): RT=2.03 min, M+H+=288.

1. custompartitioned between water (50 mL) and dichloromethane (50 mL)
2. customThe organic phase was separated
3. washwashed with saturated aqueous sodium carbonate (50 mL)
4. dry with materialdried over anhydrous sodium sulfate
5. filtrationfiltered
6. customevaporated in vacuo
7. washwas washed with methanol

ORD record

ord-993b215ad29f423486b10442a276aef6

Source dataset

uspto-grants-2013_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08501765B2