lithium aluminium tetrahydride in tetrahydrofuran T=0 - 20°C;

1: 1-(3-bromopropyl)-4-(3-chlorophenyl)-piperazine With sodium hydride in 1,4-dioxane 1 h; Reflux; 2: 1,2,4-Triazolo[4,3-a]pyridin-3(2H)-one in 1,4-dioxane 20 h; Reflux;

1.1: 1,1'-binaphthyl-2,2'-diol; potassium phosphate; copper(I) bromide / N,N-dimethyl-formamide / 24 h / 100 °C 2.1: trifluoroacetic acid / dichloromethane / 2 h / 20 °C 3.1: sodium hydride / tetrahydrofuran / 20 h / 20 °C 4.1: sodium hydride / 1,4-dioxane / 1 h / |Reflux 4.2: 20 h / |Reflux View Scheme

1.1: trifluoroacetic acid / dichloromethane / 2 h / 20 °C 2.1: sodium hydride / tetrahydrofuran / 20 h / 20 °C 3.1: sodium hydride / 1,4-dioxane / 1 h / |Reflux 3.2: 20 h / |Reflux View Scheme

hydrogenchloride in water; acetone pH=3 - 4; Product distribution / selectivity;