(2S,3S,6S)-6-Ethyl-3-nitro-2-phenyl-piperidine HBr salt → 6-Ethyl-2-phenyl-piperidin-3-ylamine

Participants

Reaction Steps

To a 250 ml Parr bottle was charged 1 gm (3.18 mmol) of the (2S,3S,6S)-6-Ethyl-3-nitro-2-phenyl-piperidine HBr salt prepared above in 60 ml of methanol. To the resulting solutionwas added an excess of commercial Raney nickel which had been exhaustively washed with deionized water until the supernatant was pH 7.00. The reaction mixture was placed under 50 p.s.i. in a Parr Hydrogenator and shaken for 4 hrs. The reaction mixture was filtered through celite and the filtrate was evaporated in vacuo. The residue was partitioned between methylene chloride and 1N NaOH. The combined organics were washed with brine and then dried and evaporated to afford 0.47 gm (72%) of crude racemic 6-Ethyl-2-phenyl-piperidin-3-ylamine. Such racemate was resolved through the formation of a salt with (−)-O,O′-dibenzoyl-L-tartaric acid in isopropanol water. 1H NMR (CDCl3, 400 MHz) δ 7.4–7.2 (br.m, 5H), 4.05 (d), 3.0 (br.t), 2.90 (m), 1.98 (m), 1.75 (m), 1.6–1.4 (m), 0.80 (t, 3H), ppm. Mass spectra m/z=205 (p+1).

Provenance & Evidence