hydrogen; palladium(II) oxide hydrate; acetic acid T=20°C; P=3675.37 Torr; 24 h;

hydrogenchloride; hydrogen; palladium 10 on activated carbon in water T=45°C; P=7500.75 Torr; 6 h;

1: 2,3-dihydro-7,8-dimethoxy-2-oxo-1H-3-benzazepine With potassium tert-butylate in dimethyl sulfoxide T=20°C; 0.5 h; 2: 3-chloro-N-{[(7S)-3,4-dimethoxybicyclo[4.2.0]octa-1,3,5-trien-7-yl]methyl}-N-methyl-1-propanamine in dimethyl sulfoxide T=20°C;

potassium carbonate in N,N-dimethyl-formamide T=25 - 45°C; 12 h;

1: [{(7S)-3,4-dimethoxybicyclo[4.2.0]octa-1,3,5-trien-7-yl}methyl](methyl)amine d-camphorsulfonate With sodium hydroxide in ethyl acetate 2: 7,8-dimethoxy-3-(3-iodopropyl)-1,3-dihydro-2H-3-benzazepin-2-one With potassium carbonate in acetone 18 h; Reflux;

potassium carbonate in acetone T=55 - 58°C; 3 h;

1: With potassium carbonate in water 0.0833333 h; 2: With hydrogenchloride in water Inert atmosphere;

1.1: potassium hydroxide; water / 4 h / Reflux 1.2: 20 °C 2.1: ethyl acetate / 1.25 h / 0 °C / Reflux 3.1: hydrogenchloride / dichloromethane; water / 0.08 h 4.1: oxalyl dichloride / N,N-dimethyl-formamide / dichloromethane / 15 - 25 °C 5.1: dichloromethane; water / 0 - 10 °C 6.1: borane-THF / tetrahydrofuran / 20 - 50 °C 6.2: 0.25 h / 0 - 5 °C 6.3: 2.5 h / 0 °C / Reflux 7.1: potassium carbonate; sodium iodide / 1-methyl-pyrrolidin-2-one / 20 - 60 °C / Inert atmosphere 7.2: 2 h / 20 °C 8.1: potassium carbonate / water / 0.08 h 8.2: Inert atmosphere View Scheme

1.1: n-butyllithium / hexane; tetrahydrofuran / -10 °C / Inert atmosphere 2.1: potassium hydroxide; water / 4 h / Reflux 2.2: 20 °C 3.1: ethyl acetate / 1.25 h / 0 °C / Reflux 4.1: hydrogenchloride / dichloromethane; water / 0.08 h 5.1: oxalyl dichloride / N,N-dimethyl-formamide / dichloromethane / 15 - 25 °C 6.1: dichloromethane; water / 0 - 10 °C 7.1: borane-THF / tetrahydrofuran / 20 - 50 °C 7.2: 0.25 h / 0 - 5 °C 7.3: 2.5 h / 0 °C / Reflux 8.1: potassium carbonate; sodium iodide / 1-methyl-pyrrolidin-2-one / 20 - 60 °C / Inert atmosphere 8.2: 2 h / 20 °C 9.1: potassium carbonate / water / 0.08 h 9.2: Inert atmosphere View Scheme

1.1: ethyl acetate / 1.25 h / 0 °C / Reflux 2.1: hydrogenchloride / dichloromethane; water / 0.08 h 3.1: oxalyl dichloride / N,N-dimethyl-formamide / dichloromethane / 15 - 25 °C 4.1: dichloromethane; water / 0 - 10 °C 5.1: borane-THF / tetrahydrofuran / 20 - 50 °C 5.2: 0.25 h / 0 - 5 °C 5.3: 2.5 h / 0 °C / Reflux 6.1: potassium carbonate; sodium iodide / 1-methyl-pyrrolidin-2-one / 20 - 60 °C / Inert atmosphere 6.2: 2 h / 20 °C 7.1: potassium carbonate / water / 0.08 h 7.2: Inert atmosphere View Scheme