Sodium Hydroxide → 4-Cyclohexylpiperidine

Participants

Reaction Steps

A solution of 4-phenylpyridine hydrochloride (4.50 g, 29.0 mmol, 1.00 equiv) in denatured EtOH (100 mL, 5% isopropanol) was stirred at 110-120° C. in the presence of 10% Pd on activated carbon (4.50 g, Aldrich) and hydrogen at 440 psi for 24 hours. The catalyst was filtered out by use of Celite and washed with CH2Cl2 (100 mL) and MeOH (150 mL). The filtrate was concentrated to give 5.32 g (90%) of white solid, which was characterized spectroscopically as 4-cyclohexylpiperidine hydrochloride. This white solid was taken up in water (150 mL), which was basified to pH 10 by addition of 1 N NaOH and extracted with CH2Cl2 (3×200 mL). The combined organic solutions were dried over MgSO4 and concentrated to afford 4.27 g of white solid (88%), which was characterized spectroscopically.

Provenance & Evidence