piperidine; pyridine T=80°C; 48 h;

1: 40 percent / HBr / diazotization 2: 1.) Mg / 1.) ether, 2.) ether, reflux, 2 h; room temp., overnight 3: 98.5 percent / LiAlH4 / diethyl ether / 1.) reflux, 3 h, 2.) room temp., overnight 4: 80.1 percent / PCC / CH2Cl2 / 2 h / Ambient temperature 5: 90.7 percent / pyridine, piperidine / 48 h / 80 °C View Scheme

1: 1.) Mg / 1.) ether, 2.) ether, reflux, 2 h; room temp., overnight 2: 98.5 percent / LiAlH4 / diethyl ether / 1.) reflux, 3 h, 2.) room temp., overnight 3: 80.1 percent / PCC / CH2Cl2 / 2 h / Ambient temperature 4: 90.7 percent / pyridine, piperidine / 48 h / 80 °C View Scheme

1: 98.5 percent / LiAlH4 / diethyl ether / 1.) reflux, 3 h, 2.) room temp., overnight 2: 80.1 percent / PCC / CH2Cl2 / 2 h / Ambient temperature 3: 90.7 percent / pyridine, piperidine / 48 h / 80 °C View Scheme

1: 80.1 percent / PCC / CH2Cl2 / 2 h / Ambient temperature 2: 90.7 percent / pyridine, piperidine / 48 h / 80 °C View Scheme