1: Ph3P; diisopropyl azodicarboxylate / tetrahydrofuran / 2 h / 20 °C 2: H2; AcOH / Pd(OH)2/C / ethyl acetate / 12 h View Scheme

1.1: 4-(N,N-dimethlyamino)pyridine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 24 h / 20 °C 2.1: sodium hydride / tetrahydrofuran / 1 h / |Reflux 3.1: potassium carbonate / acetone / 0.17 h 3.2: 2 h / 50 °C 4.1: copper dichloride; chloro-trimethyl-silane / acetonitrile / 0.5 h / 20 °C 5.1: Lindlar's catalyst; ammonium formate / methanol; ethyl acetate / 0.67 h / 50 °C 6.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 1 h / 20 °C 7.1: hydrogenchloride; water / tetrahydrofuran / 5 h / |Reflux 8.1: tetrakis(triphenylphosphine) palladium(0) / tetrahydrofuran / 0.17 h / 20 °C / |Inert atmosphere 9.1: sodium acetate / acetic anhydride / 6 h / 170 °C / |Microwave irradiation 9.2: 0.5 h / 20 °C View Scheme

piperazine in N,N-dimethyl acetamide T=150°C; Substitution; 0.5 h;