triethylamine in benzene 1 h; Ambient temperature;

1: 98 percent / NaH / tetrahydrofuran / 18 h / 80 °C 2: 96 percent / H2 / 10percent Pd/C / benzene / 4 h / 3040 Torr / Ambient temperature 3: 85 percent / triethylamine / benzene / 1 h / Ambient temperature View Scheme

1: 96 percent / H2 / 10percent Pd/C / benzene / 4 h / 3040 Torr / Ambient temperature 2: 85 percent / triethylamine / benzene / 1 h / Ambient temperature View Scheme

1: 79 percent / HCl(g) / ethanol / 0.5 h / Heating 2: 98 percent / NaH / tetrahydrofuran / 18 h / 80 °C 3: 96 percent / H2 / 10percent Pd/C / benzene / 4 h / 3040 Torr / Ambient temperature 4: 85 percent / triethylamine / benzene / 1 h / Ambient temperature View Scheme