HCID 59442134, compound → HCID 59441972, compound

Participants

Reaction Steps

A solution of 1-(3-ethenyl-4-nitrophenyl)-4-(1-methylethyl)piperazine (1.4 g, 5.1 mmol) and 10% palladium on carbon (0.5 g) in degassed ethanol was maintained under an atmosphere of hydrogen (60 psi) overnight. The next morning, the reaction was filtered through celite, concentrated, and purified via chromatography on SiO2 to afford 2-ethyl-4-[4-(1-methylethyl)-1-piperazinyl]aniline (0.8 g, 3.2 mmol, 64% Yield). 1H NMR (400 MHz, CDCl3) d ppm 0.92 (t, J=7.3 Hz, 3 H), 1.51-1.60 (m, 2 H), 1.81 (dd, J=7.7, 2.9 Hz, 4 H), 1.98-2.06 (m, 2 H), 2.30-2.37 (m, 2 H), 2.40 (t, J=7.9 Hz, 1 H), 3.06 (d, J=11.7 Hz, 2 H), 3.67 (s, 2 H), 3.82 (s, 3 H), 6.63-6.70 (m, 3 H). 1 H NMR (400 MHz, DMSO-d6) δ ppm 0.96 (d, J=6.6 Hz, 6 H), 1.07 (td, J=7.5, 0.7 Hz, 3H), 2.37 (q, J=7.3 Hz, 2 H), 2.51 (s, 4 H), 2.59-2.67 (m, 1 H), 2.86 (s, 4 H), 4.29 (s, 2 H), 6.48 (s, 1H), 6.51 (d, J=19.0 Hz, 2 H).

Provenance & Evidence