1: With AlCl3, aluminium chloride; thiourea in toluene T=60 - 65°C; 2: With ammonia in water; toluene T=15 - 30°C; pH=8 - 9; 3: With hydrogenchloride in dichloromethane

hydrogenchloride in ethyl acetate; isopropyl alcohol T=0 - 20°C; 3 h;

1: (S)-1,2,3,4-tetrahydro-5-hydroxy-N-propyl-naphthalen-2-ammonium hydrobromide With sodium carbonate in o-xylene; water T=70 - 80°C; 2: [2-(thien-2-yl)ethyl] 4-methylbenzenesulfonate With sodium carbonate in o-xylene Reflux; 3: With hydrogenchloride in o-xylene; water; isopropyl alcohol; toluene T=15 - 55°C;

1: With AlCl3, aluminium chloride; thiourea in toluene T=100 - 105°C; 3 h; 2: With ammonia in water; toluene T=20 - 25°C; pH=8 - 9; 3: With hydrogenchloride in toluene T=20°C; Reflux;

1.1: sodium acetate; acetic acid; sodium tris(acetoxy)borohydride / tetrahydrofuran / 0 - 10 °C 1.2: 0.5 h / 0 - 20 °C 1.3: 1.33 h / 10 - 50 °C 2.1: potassium carbonate / 2-methyl tetrahydrofuran / Reflux 3.1: methyltretrahydrofuran, 2- / 75 °C 4.1: hydrogenchloride / water; tetrahydrofuran / 0.25 h / 65 °C 5.1: sodium hydrogensulfite; water; hydrogen bromide; acetic acid / 2 h / Reflux 6.1: sodium carbonate / o-xylene; water / 70 - 80 °C 6.2: Reflux 6.3: 15 - 55 °C View Scheme

1.1: lauryl mercaptan / ethyl acetate / Inert atmosphere; Reflux 1.2: 0.58 h / Inert atmosphere; Reflux 1.3: 0.08 h / Reflux 2.1: potassium carbonate / 2-methyl tetrahydrofuran / Reflux 3.1: methyltretrahydrofuran, 2- / 75 °C 4.1: hydrogenchloride / water; tetrahydrofuran / 0.25 h / 65 °C 5.1: sodium hydrogensulfite; water; hydrogen bromide; acetic acid / 2 h / Reflux 6.1: sodium carbonate / o-xylene; water / 70 - 80 °C 6.2: Reflux 6.3: 15 - 55 °C View Scheme

1.1: potassium carbonate / 2-methyl tetrahydrofuran / Reflux 2.1: methyltretrahydrofuran, 2- / 75 °C 3.1: hydrogenchloride / water; tetrahydrofuran / 0.25 h / 65 °C 4.1: sodium hydrogensulfite; water; hydrogen bromide; acetic acid / 2 h / Reflux 5.1: sodium carbonate / o-xylene; water / 70 - 80 °C 5.2: Reflux 5.3: 15 - 55 °C View Scheme

1.1: methyltretrahydrofuran, 2- / 75 °C 2.1: hydrogenchloride / water; tetrahydrofuran / 0.25 h / 65 °C 3.1: sodium hydrogensulfite; water; hydrogen bromide; acetic acid / 2 h / Reflux 4.1: sodium carbonate / o-xylene; water / 70 - 80 °C 4.2: Reflux 4.3: 15 - 55 °C View Scheme

1.1: hydrogen bromide / Inert atmosphere; Reflux 2.1: potassium carbonate / dichloromethane; water / 5 - 10 °C 3.1: sodium tetrahydroborate / toluene / 1 h / 20 - 25 °C / Inert atmosphere 3.2: 8 h / 80 - 90 °C / Inert atmosphere 4.1: hydrogenchloride / ethanol; water View Scheme

1.1: triethylamine / toluene / 4 h / 45 °C 2.1: sodium carbonate / o-xylene; water / 70 - 80 °C 2.2: Reflux 2.3: 15 - 55 °C View Scheme