potassium hydroxide in water T=120°C; 15 h;

1: 90 percent / piperidine / benzene / Heating 2: 1.) Zn, dibromoethane / 1.) THF, 70 deg C, 15 deg C, 2 h; 2.) THF, roomtemperature, 15 h 3: KOH / H2O / 15 h / 120 °C View Scheme

1: 1.) Zn, dibromoethane / 1.) THF, 70 deg C, 15 deg C, 2 h; 2.) THF, roomtemperature, 15 h 2: KOH / H2O / 15 h / 120 °C View Scheme

1: Cu / 6 h / 180 °C 2: 1.) SOCl2 / 1.) 150 deg C, 1 h; 2.) benzene 4-5 h 3: 80 percent / LiAlH4 / diethyl ether / 15 h / Heating 4: 1 M NaOCl / CH2Cl2 / 1.5 h 5: 92 percent / 15 percent TiCl3 / acetic acid; H2O / -10 °C 6: methanol / 8 h / Heating View Scheme