hydrogen; nickel in ethanol P=258.6 Torr; 1 h;

methylamine in ethanol 12 h; Ambient temperature;

1: 36 percent / 4-(dimethylamino)pyridine, pyridine / CH2Cl2 / 24 h / Ambient temperature 2: 45 percent / sodium azide / dimethylformamide / 30 h / 80 - 90 °C 3: 0.7 g / H2 / Raney Ni / ethanol / 1 h / 258.6 Torr View Scheme

1: 45 percent / sodium azide / dimethylformamide / 30 h / 80 - 90 °C 2: 0.7 g / H2 / Raney Ni / ethanol / 1 h / 258.6 Torr View Scheme

in ethanol; dichloromethane

1: 57 percent / sodium azide, acetic acid / dimethylsulfoxide / 90 h / 72 °C 2: 60 percent / 40 percent aq. methylamine / ethanol / 12 h / Ambient temperature View Scheme