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

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Reaction Steps

tert-Butyl 7-(2-oxo-4-phenethylpiperazin-1-yl)-3,4-dihydro-1H-pyrido[4,3-b]indole-2(5H)-carboxylate (160 mg, 0.337 mmol) was deprotected and converted to the dihydrochloride salt according to Example 2 (step f) to provide the title compound (110 mg, 73%) as a white solid: 1H NMR (500 MHz, DMSO-d6) δ 12.06 (s, 1H), 11.35 (s, 1H), 9.35 (s, 2H), 7.49 (d, J=8.3 Hz, 1H), 7.41-7.23 (m, 6H), 6.97-6.94 (dd, J=8.3, 1.7 Hz, 1H), 4.30 (s, 2H), 4.24-3.97 (m, 3H), 3.96-3.73 (m, 2H), 3.63-3.27 (m, 5H), 3.23-3.08 (m, 2H), 3.08-2.98 (m, 2H); ESI MS m/z 375 [M+H]+; HPLC (Method B) 98.8% (AUC), tR=11.2 min.

Provenance & Evidence