1: 3-[2-(1,3-dioxolan-2-yl)ethyl]-7,8-dimethoxy-1,3-dihydro-2H-3-benz-azepin-2-one With hydrogen; palladium on activated charcoal in ethanol T=55°C; P=3750.38 Torr; 2: 1-[(7S)-3,4-dimethoxybicyclo[4.2.0]octa-1,3,5-trien-7-yl]-N-methylmethanamine hydrochloride in ethanol; water T=20 - 85°C; P=22502.3 Torr;

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

hydrogenchloride in diethyl ether; acetonitrile Product distribution / selectivity;

1: 7,8-dimethoxy-2-oxo-2,3,4,5-tetrahydro-1H-3-benzazepine With potassium tert-butylate in dimethyl sulfoxide 1.08333 h; Inert atmosphere; 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=25 - 30°C; 3: With hydrogenchloride in isopropyl alcohol; acetonitrile T=15 - 20°C; pH=1 - 2; 12 h; 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 9.1: hydrogenchloride; hydrogen / palladium 10 on activated carbon / water / 6 h / 45 °C / 7500.75 Torr 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 8.1: hydrogenchloride; hydrogen / palladium 10 on activated carbon / water / 6 h / 45 °C / 7500.75 Torr View Scheme

1.1: potassium hydroxide / water / 4 h 1.2: 0.5 h / Cooling with ice-water bath 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 9.1: hydrogenchloride; hydrogen / palladium 10 on activated carbon / water / 6 h / 45 °C / 7500.75 Torr 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 10.1: hydrogenchloride; hydrogen / palladium 10 on activated carbon / water / 6 h / 45 °C / 7500.75 Torr View Scheme

1: With potassium carbonate; sodium iodide in acetone T=20 - 65°C; 2: With triethylamine; acetyl chloride in toluene 3: With hydrogenchloride in water; toluene pH=2 - 3; Product distribution / selectivity;

1.1: potassium carbonate / 20 °C 2.1: potassium tert-butylate / dimethyl sulfoxide / 1 h / 20 °C 2.2: 20 °C 3.1: hydrogenchloride / diethyl ether; acetonitrile View Scheme