1: With sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate T=65°C; Alkylation; 5 h; 2: With hydrogenchloride in methanol; dichloromethane T=20°C; deprotection; 2 h;

1.1: KOH / benzene / 23 h / Heating 1.2: 53 percent / p-TsOH / methanol; CH2Cl2 / 5 h / 20 °C 2.1: aq. NaOH (50 percent); Bu4N(1+)*HSO4(1-) / 5 h / 65 °C 2.2: 34 percent / conc. HCl / methanol; CH2Cl2 / 2 h / 20 °C View Scheme

1: 56 percent / NaOH / dioxane / 18 h / 80 °C 2: hydrogen, p-toluenesulphonic acid / Pd/C / 25 °C / 7500.6 Torr View Scheme

1: 52 percent / KOH / dioxane / 18 h / 80 °C 2: hydrogen, p-toluenesulphonic acid / Pd/C / 25 °C / 7500.6 Torr View Scheme

sodium hydroxide in 1,4-dioxane T=80°C; 18 h;

potassium hydroxide in 1,4-dioxane T=80°C; 18 h;