hydrogen; nickel in methanol T=100°C; 8 h;

1: 97 percent / glacial CH3COOH, H2O / tetrahydrofuran / 18 h / 70 °C 2: 90 percent / H2 / Raney Ni / methanol / 8 h / 100 °C View Scheme

1: 1.) morpholine, 80 deg C, 1 h, 2.) morpholine, water, 100 deg C, 1 h 2: 98 percent / CH3ONa / tetrahydrofuran / 20 h / Ambient temperature 3: 97 percent / glacial CH3COOH, H2O / tetrahydrofuran / 18 h / 70 °C 4: 90 percent / H2 / Raney Ni / methanol / 8 h / 100 °C View Scheme

1: 98 percent / CH3ONa / tetrahydrofuran / 20 h / Ambient temperature 2: 97 percent / glacial CH3COOH, H2O / tetrahydrofuran / 18 h / 70 °C 3: 90 percent / H2 / Raney Ni / methanol / 8 h / 100 °C View Scheme