1,4-diaza-bicyclo[2.2.2]octane; palladium diacetate in DMF (N,N-dimethyl-formamide) T=105°C; Heck Reaction; 3 h;

1.1: tert.-butyl lithium / hexane; tetrahydrofuran / 0.5 h / -78 °C 1.2: 4 h / -78 - 20 °C 2.1: hydrogenchloride / methanol / water / 5 h / 110 °C 3.1: 1,4-diaza-bicyclo[2.2.2]octane / palladium diacetate / N,N-dimethyl-formamide / 3 h / 110 °C / Inert atmosphere View Scheme

1: hydrogenchloride / methanol / water / 5 h / 110 °C 2: 1,4-diaza-bicyclo[2.2.2]octane / palladium diacetate / N,N-dimethyl-formamide / 3 h / 110 °C / Inert atmosphere View Scheme

1.1: triethylamine / dichloromethane / 16 h / 20 °C 2.1: tert.-butyl lithium / hexane; tetrahydrofuran / 0.5 h / -78 °C 2.2: 4 h / -78 - 20 °C 3.1: hydrogenchloride / methanol / water / 5 h / 110 °C 4.1: 1,4-diaza-bicyclo[2.2.2]octane / palladium diacetate / N,N-dimethyl-formamide / 3 h / 110 °C / Inert atmosphere View Scheme

hydrogenchloride T=0°C; 16.5 h; Reflux;