Sodium → 4-(Piperidin-4-yl)benzoic acid

Participants

Reaction Steps

To the sodium salt of 4-pyridine benzoic acid (500 mg, 2.25 mmol) suspended in 20% AcOH/MeOH (20 ml) was added PtO2 (250 mg) and the mixture was hydrogenated at 50 psi with agitation (Parr) for 4 h. The solution was filtered through celite, washed with MeOH (3×5 ml), evaporated with hexane (4×) to azeotrope the acetic acid. TLC of the crude (EtOH/H2O/NH4OH 10:1:1) shows no starting material, but did show 2 more polar spots. After evaporation from hexane, the white solid (596 mg crude, still with residual HOAc) was dried in a vacuum overnight, and used without further purification in subsequent steps. MS m/z [M+H]+.

Provenance & Evidence