Tetrafluoro-m-phenylenediamine dihydrochloride → 4-(4-Fluorophenethyl)-1-(5-methyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indol-7-yl)piperazin-2-one dihydrochloride

Participants

Reaction Steps

tert-Butyl 7-(4-(4-fluorophenethyl)-2-oxopiperazin-1-yl)-5-methyl-3,4-dihydro-1H-pyrido[4,3-b]indole-2(5H)-carboxylate (730 mg, 1.44 mmol) was deprotected and converted to the dihydrochloride according to Example 2 (step g) to provide the title compound (433 mg, 63%) as a white solid: 298° C. dec; 1H NMR (500 MHz, DMSO-d6) δ 12.32 (s, 1H), 9.53 (s, 2H), 7.53 (d, J=8.3 Hz, 1H), 7.42 (d, J=8.3 Hz, 1H), 7.39-7.34 (m, 2H), 7.20 (t, J=8.8 Hz, 2H), 7.02-7.00 (dd, J=8.3, 1.6 Hz, 1H), 4.38 (s, 2H), 4.27-4.19 (m, 1H), 4.19-3.99 (m, 2H), 3.94-3.81 (m, 2H), 3.66 (s, 3H), 3.64-3.54 (m, 1H), 3.54-3.33 (m, 4H), 3.19-3.11 (m, 2H), 3.10-3.05 (m, 2H); ESI MS m/z 407 [M+H]+; HPLC (Method B)>99% (AUC), tR=11.9 min.

Provenance & Evidence