potassium iodide in water; N,N-dimethyl-formamide T=90°C; 4.5 h;

1: 96 percent / LiAlH4 / diethyl ether / 3 h / Heating 2: 81 percent / pyridine / 4 h / 0 °C 3: 82 percent / KI / H2O; dimethylformamide / 4.5 h / 90 °C View Scheme

1: 95 percent / benzoic acid, piperidine / benzene / 23 h / Heating 2: 1.) Mg, I2 / 1.) ether, reflux, 1 h, 2.) ether, reflux, 4h; benzene, reflux, overnight 3: 96 percent / LiAlH4 / diethyl ether / 3 h / Heating 4: 81 percent / pyridine / 4 h / 0 °C 5: 82 percent / KI / H2O; dimethylformamide / 4.5 h / 90 °C View Scheme

1: 1.) Mg, I2 / 1.) ether, reflux, 1 h, 2.) ether, reflux, 4h; benzene, reflux, overnight 2: 96 percent / LiAlH4 / diethyl ether / 3 h / Heating 3: 81 percent / pyridine / 4 h / 0 °C 4: 82 percent / KI / H2O; dimethylformamide / 4.5 h / 90 °C View Scheme

potassium hydroxide in ethylene glycol 5 h; Heating;