1: anhydrous 3-(dimethylamino)propyltriphenylphosphonium bromide hydrobromide With sodium hydride in tetrahydrofuran Wittig Reaction; 3 h; Heating / reflux; 2: (11-oxo-6,11-dihydro-dibenzo[b,e]oxepin-2-yl)-acetic acid benzyl ester in tetrahydrofuran T=0 - 30°C; 3 h; 3: With hydrogenchloride; water in di-isopropyl ether pH=2;

hydrogenchloride in water; acetone T=5 - 25°C; 2 - 15 h; Product distribution / selectivity;

hydrogenchloride in chlorobenzene T=80 - 85°C; 5 h;

1: in tetrahydrofuran T=20°C; Grignard Reaction; Inert atmosphere; 2: With ammonium chloride in tetrahydrofuran; water 3: With hydrogenchloride in tetrahydrofuran; water T=20°C; pH=~ 1; 17.75 h; Reflux;

1: With water; sodium hydroxide in methanol 2 h; Reflux; 2: With hydrogenchloride in water pH=2;

hydrogenchloride; water in acetone 10 h; Reflux; Product distribution / selectivity;

1: anhydrous 3-(dimethylamino)propyltriphenylphosphonium bromide hydrobromide With sodium hydride in tetrahydrofuran; mineral oil T=65°C; Inert atmosphere; 2: 6,11-dihydro-11-oxo-dibenz[b,e]oxepine-2-acetic acid in tetrahydrofuran; mineral oil T=20°C; Wittig Reaction; 15 h; 3: With hydrogenchloride in tetrahydrofuran; water; mineral oil pH=2.27; Product distribution / selectivity;

1: With hydrogenchloride in water T=25 - 95°C; 2: With acetic acid in water T=25 - 30°C; Purification / work up;

1: 1-dimethylamino-3-chloropropane With iodine; magnesium; ethylene dibromide in tetrahydrofuran 1 h; Inert atmosphereReflux; 2: 6,11-dihydro-11-oxo-dibenz[b,e]oxepine-2-acetic acid in tetrahydrofuran T=5 - 30°C; 3: With hydrogenchloride; acetic acid in tetrahydrofuran; water T=25 - 30°C; Product distribution / selectivity;

1.1: potassium carbonate / N,N-dimethyl-formamide / 4 h / 25 °C 2.1: iodine; silver sulphate / methanol / 2 h / 18 °C 3.1: copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride; triethylamine / N,N-dimethyl-formamide / 5 h / 25 °C / Inert atmosphere 4.1: piperidine; formic acid; palladium diacetate; tris-(o-tolyl)phosphine / N,N-dimethyl-formamide / 3 h / 92 °C / Inert atmosphere 5.1: pyridine / 5 - 20 °C 6.1: methanol; water / 3 h / Reflux 7.1: water; sodium hydroxide / methanol / 2 h / Reflux 7.2: pH 2 View Scheme