hydrogen bromide in water T=85 - 90°C; 15 h;

sulfuric acid; hydrogen bromide in water T=25 - 55°C;

1.1: pyridine; piperidine / 4.25 h / 20 - 120 °C / |Inert atmosphere 1.2: pH 2 2.1: sodium hydroxide / water / 20 °C 2.2: 7 h / 25 - 30 °C / 750.08 Torr 2.3: pH 2 3.1: thionyl chloride / 4 h / |Inert atmosphere; |Reflux 4.1: sodium tetrahydroborate / tetrahydrofuran / |Inert atmosphere; |Reflux 4.2: 9 h / 60 - 65 °C / |Inert atmosphere 5.1: hydrogen bromide / water / 15 h / 85 - 90 °C View Scheme

1.1: sodium hydroxide / water / 20 °C 1.2: 7 h / 25 - 30 °C / 750.08 Torr 1.3: pH 2 2.1: thionyl chloride / 4 h / |Inert atmosphere; |Reflux 3.1: sodium tetrahydroborate / tetrahydrofuran / |Inert atmosphere; |Reflux 3.2: 9 h / 60 - 65 °C / |Inert atmosphere 4.1: hydrogen bromide / water / 15 h / 85 - 90 °C View Scheme

1.1: thionyl chloride / 4 h / |Inert atmosphere; |Reflux 2.1: sodium tetrahydroborate / tetrahydrofuran / |Inert atmosphere; |Reflux 2.2: 9 h / 60 - 65 °C / |Inert atmosphere 3.1: hydrogen bromide / water / 15 h / 85 - 90 °C View Scheme

1.1: sodium tetrahydroborate / tetrahydrofuran / |Inert atmosphere; |Reflux 1.2: 9 h / 60 - 65 °C / |Inert atmosphere 2.1: hydrogen bromide / water / 15 h / 85 - 90 °C View Scheme

1: (R)-(+)-1-(1-naphthyl)-ethylamine; benzaldehyde T=25 - 30°C; 2: 1-(3-bromopropyl)-3-(trifluoromethyl)benzene in 1-methyl-pyrrolidin-2-one T=130 - 140°C; 12 h; 3: With hydrogenchloride; water in 1-methyl-pyrrolidin-2-one; toluene pH=0.5 - 2;

1: (R)-(+)-1-(1-naphthyl)-ethylamine With benzaldehyde T=25 - 30°C; Forster reaction; 2: 1-(3-bromopropyl)-3-(trifluoromethyl)benzene in 1-methyl-pyrrolidin-2-one T=125 - 130°C; Forster reaction; Further stages;

1: With potassium iodide T=120 - 130°C; 2: With hydrogenchloride; water in acetonitrile T=25 - 35°C; pH=1 - 2; 1 h; 3: With ammonia in water pH=9 - 10; Product distribution / selectivity;

potassium carbonate in dichloromethane T=38°C; 1.25 h; Product distribution / selectivity;