Water → 4-(N-piperidinomethylcarbonyl-N-methyl-amino)-aniline

Participants

Reaction Steps

A mixture of 3.12 g (11.3 mmol) of N-Methyl-N-(4-nitrophenyl)-2-piperidin-1-yl-acetamide, 2.52 g (45.1 mmol) of Fe powder and 2.99 g (56.5 mmol) of NH4Cl in 65 mL of MeOH+25 mL of H2O is stirred and refluxed for 3.5 h. The cooled reaction is filtered, the precipitate is washed with MeOH and the filtrate and wash were combined and evaporated. The residue is redissolved in H2O, neutralized with K2CO3 and extracted with EtOAc. The combined extracts were treated with Darco, dried (MgSO4), evaporated and dried in vacuo to give 2.36 g (85%) of brown oil. 1H NMR (DMSO-d6 δ 6.85 (d, 2H, J=7.1 Hz), 6.51 (d, 2H, J=7.1 Hz), 3.30 (s, 2H), 2.78 (s, 3H), 2.24 (s, 4H), 1.50 (m, 6H); MS (ESI) m/z 248.0 (M+H).

Provenance & Evidence