3-Chloro-N-ethyl-4-(piperazin-1-yl)benzamide → 3-Chloro-4-(4-((8-ethoxy-2-methyl-3-oxo-3,4-dihydro-2H-benzo[b][1,4]oxazin-6-yl)methyl)piperazin-1-yl)-N-ethylbenzamide

Participants

Reaction Steps

Using 398B and 3-chloro-N-ethyl-4-(piperazin-1-yl)benzamide 286 in the general procedure for reductive aminations, the title compound was obtained as a white solid: 1H NMR (400 MHz, DMSO-d6) δ ppm 1.11 (t, J=7.20 Hz, 3H) 1.29-1.38 (m, 3H) 1.38-1.47 (m, 3H) 2.52-2.59 (m, 4H) 3.05 (br. s., 4H) 3.20-3.31 (m, 2H) 3.43 (s, 2H) 3.99-4.09 (m, 2H) 4.55-4.65 (m, 1H) 6.51 (d, J=1.77 Hz, 1H) 6.60-6.67 (m, 1H) 7.19 (d, J=8.59 Hz, 1H) 7.77 (dd, J=8.59, 2.02 Hz, 1H) 7.88 (d, J=2.02 Hz, 1H) 8.44 (t, J=5.56 Hz, 1H) 10.58 (s, 1H). ESI-MS: m/z 487.4 (M+H)+. mp 186.6-198.7° C.

Provenance & Evidence