hydrogenchloride in 1,4-dioxane T=80°C; 6 h;

1: 88 percent / H2 / 10percent Pd/C / aq. NaOH / 15 h / 760 Torr / Ambient temperature 2: 98 percent / potassium carbonate / acetone / 3 h / Heating 3: 1.) sodium hydride / 1.) benzene, 80 deg C, 1 h, 2.) benzene, a) 35 deg C, b) 45 to 50 deg C, 1 h 4: 68 percent / piperidine / toluene / 5 h / Heating 5: 95 percent / 0.2 N HCl / dioxane / 6 h / 80 °C View Scheme

1: 98 percent / potassium carbonate / acetone / 3 h / Heating 2: 1.) sodium hydride / 1.) benzene, 80 deg C, 1 h, 2.) benzene, a) 35 deg C, b) 45 to 50 deg C, 1 h 3: 68 percent / piperidine / toluene / 5 h / Heating 4: 95 percent / 0.2 N HCl / dioxane / 6 h / 80 °C View Scheme

1: 1.) sodium hydride / 1.) benzene, 80 deg C, 1 h, 2.) benzene, a) 35 deg C, b) 45 to 50 deg C, 1 h 2: 68 percent / piperidine / toluene / 5 h / Heating 3: 95 percent / 0.2 N HCl / dioxane / 6 h / 80 °C View Scheme

1: 68 percent / piperidine / toluene / 5 h / Heating 2: 95 percent / 0.2 N HCl / dioxane / 6 h / 80 °C View Scheme