Hydrochloric Acid → 3-Aminomethyl-1-(p-chlorobenzyl)piperidine

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3-Carbamoyl-1-(4-chlorobenzyl)piperidine (3.80 g, 15 mmol) was dissolved in THF (30 mL), and 1 M BH3-THF (9.4 mL) was added to the obtained solution. The resulting mixture was stirred at 70° C. for 15 hours. After cooling to 0° C., a 2 M hydrochloric acid (50 mL) was added, and the mixture was stirred at room temperature for another 3 hours, basicified with an 4 M aqueous solution of NaOH and extracted with ethyl acetate (100 mL×3). The extracts were combined, washed with brine, dried over anhydrous Na2SO4, filtered and concentrated. The obtained crude product was purified by column chromatography (SiO2, ethyl acetate/ethanol/triethylamine=80:15:5) to thereby provide 3-(aminomethyl)-1-(4-chlorobenzyl)piperidine (2.05 g, 55%). 1H NMR (CDCl3, 400 MHz) δ 1.00-1.09 (m, 1H), 1.50-1.87 (m, 7H), 1.97-2.06 (m, 1H), 2.65-2.77 (m, 2H), 3.16-3.26 (m, 2H), 3.32 (s, 2H), 3.40 (d, J=13.3 Hz, 1H), 3.49 (d, J=13.3 Hz, 1H), 7.22-7.33 (m, 5H).

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