Sodium methanethiolate → 1-[2-Methyl-5-(methyloxy)-4-nitrophenyl]-4-[2-(methylthio)ethyl]piperidine

Participants

Reaction Conditions

Reaction Steps

To 4-(2-iodoethyl)-1-[2-methyl-5-(methyloxy)-4-nitrophenyl]piperidine (40.6 g, 100 mmol) was added sodium thiomethoxide (7.75 g, 111 mmol) and diluted with DMF (201 mL). The reaction was stirred at 50° C. overnight. The solution was diluted with EtOAc and washed with H2O. The organic layer was dried (MgSO4), filtered, and rotovapped down to provide the title compound of step H (33.5 g) which was used without further purification. 1H NMR (400 MHz, DMSO-d6) δ 7.72 (s, 1H), 6.64 (s, 1H), 3.86 (s, 3H), 3.23 (d, J=12.1 Hz, 2H), 2.60-2.72 (m, 2H), 2.46-2.52 (m, 2H), 2.14 (s, 3H), 2.01 (s, 3H), 1.75 (d, J=12.1 Hz, 2H), 1.50 (t, J=5.7 Hz, 3H), 1.16-1.35 (m, 2H).

Provenance & Evidence