1'-[2-Chloro-5-(methyloxy)-4-nitrophenyl]-1,4'-bipiperidine → 4-(1,4'-Bipiperidin-1'-yl)-5-chloro-2-(methyloxy)aniline

Participants

Reaction Steps

1′-[2-Chloro-5-(methyloxy)-4-nitrophenyl]-1,4′-bipiperidine was dissolved in EtOH and 5% sulfided platinum on carbon was added. The reaction was placed on a Fischer-Porter Hydrogenator under 50 psi of H2 gas and was allowed to stir at rt overnight. TLC and MS showed the reaction was complete. The catalyst was filtered off and the filtrate was concentrated in vacuo to give the title compound of step D without further purification (2.36 g, 96%). 1H NMR (400 MHz, DMSO-d6) δ ppm 6.56-6.62 (m, 2H), 4.57 (br. s, 2H), 3.70 (d, J=1.3 Hz, 3H), 3.06 (d, J=10.6 Hz, 2H), 2.52 (t, J=11.5 Hz, 2H), 2.39-2.44 (m, 4H), 2.24 (t, J=13.8 Hz, 1H), 1.70 (d, J=11.5 Hz, 2H), 1.54 (t, J=12.4 Hz, 2H), 1.41-1.48 (m, 4H), 1.30-1.38 (m, 2H).

Provenance & Evidence