1: 3-cyclobutyl-2,3,4,5-tetrahydro-1H-benzo[d]azepin-7-ol With sodium hydride in dimethyl sulfoxide; mineral oil 0.5 h; 2: 6-chloro-nicotinic acid N-methylamide in dimethyl sulfoxide; mineral oil T=120°C;

1: With acetic acid in dichloromethane T=20°C; 1 h; 2: With sodium tris(acetoxy)borohydride in dichloromethane T=0 - 20°C; 16 h; 3: With sodium hydroxide in dichloromethane; water 0.5 h;

1.1: trimethylamine / dichloromethane / 2 h / 0 °C 2.1: sodium hydride / dimethyl sulfoxide; mineral oil / 0.5 h 2.2: 120 °C View Scheme

1.1: thionyl chloride; N,N-dimethyl-formamide / toluene / 2.5 h / 20 - 100 °C 2.1: trimethylamine / dichloromethane / 2 h / 0 °C 3.1: sodium hydride / dimethyl sulfoxide; mineral oil / 0.5 h 3.2: 120 °C View Scheme

1.1: hydrogen bromide; tetra-(n-butyl)ammonium iodide / acetic acid / 100 °C 2.1: sodium hydride / dimethyl sulfoxide; mineral oil / 0.5 h 2.2: 120 °C View Scheme

1.1: acetic acid / dichloromethane / 0.5 h / 0 - 20 °C 1.2: 20 °C 2.1: hydrogen bromide; tetra-(n-butyl)ammonium iodide / acetic acid / 100 °C 3.1: sodium hydride / dimethyl sulfoxide; mineral oil / 0.5 h 3.2: 120 °C View Scheme

1.1: borane-THF / tetrahydrofuran / 0 °C / Reflux 2.1: acetic acid / dichloromethane / 0.5 h / 0 - 20 °C 2.2: 20 °C 3.1: hydrogen bromide; tetra-(n-butyl)ammonium iodide / acetic acid / 100 °C 4.1: sodium hydride / dimethyl sulfoxide; mineral oil / 0.5 h 4.2: 120 °C View Scheme

1.1: thionyl chloride; N,N-dimethyl-formamide / toluene / 15 h / 20 °C 2.1: trimethylamine / dichloromethane / 0 - 20 °C 3.1: hydrogenchloride / water; acetic acid / 20 °C 4.1: palladium 10 on activated carbon; hydrogen / acetic acid / 8 h / 3102.97 Torr 5.1: borane-THF / tetrahydrofuran / 0 °C / Reflux 6.1: acetic acid / dichloromethane / 0.5 h / 0 - 20 °C 6.2: 20 °C 7.1: hydrogen bromide; tetra-(n-butyl)ammonium iodide / acetic acid / 100 °C 8.1: sodium hydride / dimethyl sulfoxide; mineral oil / 0.5 h 8.2: 120 °C View Scheme

1.1: palladium 10 on activated carbon; hydrogen / acetic acid / 8 h / 3102.97 Torr 2.1: borane-THF / tetrahydrofuran / 0 °C / Reflux 3.1: acetic acid / dichloromethane / 0.5 h / 0 - 20 °C 3.2: 20 °C 4.1: hydrogen bromide; tetra-(n-butyl)ammonium iodide / acetic acid / 100 °C 5.1: sodium hydride / dimethyl sulfoxide; mineral oil / 0.5 h 5.2: 120 °C View Scheme

1.1: hydrogenchloride / water; acetic acid / 20 °C 2.1: palladium 10 on activated carbon; hydrogen / acetic acid / 8 h / 3102.97 Torr 3.1: borane-THF / tetrahydrofuran / 0 °C / Reflux 4.1: acetic acid / dichloromethane / 0.5 h / 0 - 20 °C 4.2: 20 °C 5.1: hydrogen bromide; tetra-(n-butyl)ammonium iodide / acetic acid / 100 °C 6.1: sodium hydride / dimethyl sulfoxide; mineral oil / 0.5 h 6.2: 120 °C View Scheme