1: in methanol T=40°C; 1.25 h; 2: With hydrogen; palladium on activated carbon in methanol T=40°C; P=5947.36 Torr; 20 h;

hydrogen; palladium 10 on activated carbon in methanol P=2068.65 - 2585.81 Torr;

5 Pd(II)/C(eggshell); hydrogen in 1,1-dimethylpropan-1-ol T=80°C; P=5171.62 Torr;

1.1: 1-methyl-piperazine / toluene / Heating 1.2: 5 h / Reflux 2.1: 5 Pd(II)/C(eggshell); hydrogen / 1,1-dimethylpropan-1-ol / 80 °C / 5171.62 Torr View Scheme

1.1: 1-methyl-piperazine / toluene / Heating 1.2: 5 h / Reflux 2.1: 5 Pd(II)/C(eggshell); hydrogen / 1,1-dimethylpropan-1-ol / 80 °C / 5171.62 Torr View Scheme

1.1: sodium tetrahydroborate / tetrahydrofuran / 0 - 35 °C / Industry scale 1.2: 5 - 30 °C / pH 1 - 2 / Industry scale 2.1: potassium carbonate / acetone / 20 - 25 °C / Industry scale 2.2: 50 - 60 °C 3.1: pyridine / dichloromethane / 5 - 30 °C / Industry scale 4.1: water / 75 - 78 °C / Industry scale 5.1: ethyl bromide; iodine; magnesium / tetrahydrofuran / 50 - 60 °C 5.2: -70 - -60 °C 5.3: -50 °C 6.1: BH3*S(CH3)2 / tetrahydrofuran / 25 - 50 °C 6.2: 0.5 h / 10 - 15 °C / Industry scale 7.1: raney nickel / methanol / 30 - 35 °C / Autoclave View Scheme

1.1: water / 75 - 78 °C / Industry scale 2.1: ethyl bromide; iodine; magnesium / tetrahydrofuran / 50 - 60 °C 2.2: -70 - -60 °C 2.3: -50 °C 3.1: BH3*S(CH3)2 / tetrahydrofuran / 25 - 50 °C 3.2: 0.5 h / 10 - 15 °C / Industry scale 4.1: raney nickel / methanol / 30 - 35 °C / Autoclave View Scheme

1.1: potassium carbonate / acetone / 20 - 25 °C / Industry scale 1.2: 50 - 60 °C 2.1: pyridine / dichloromethane / 5 - 30 °C / Industry scale 3.1: water / 75 - 78 °C / Industry scale 4.1: ethyl bromide; iodine; magnesium / tetrahydrofuran / 50 - 60 °C 4.2: -70 - -60 °C 4.3: -50 °C 5.1: BH3*S(CH3)2 / tetrahydrofuran / 25 - 50 °C 5.2: 0.5 h / 10 - 15 °C / Industry scale 6.1: raney nickel / methanol / 30 - 35 °C / Autoclave View Scheme

1.1: potassium carbonate; potassium iodide / toluene; methanol / 20 h / Reflux 2.1: methanesulfonic acid / 3 h / 100 °C 3.1: sodium tetrahydroborate / methanol / 2 h / 0 °C 3.2: 0.08 h 3.3: pH 8 View Scheme

1: feso chromenyl With titanium (IV) isopropoxide in tetrahydrofuran 1 h; Reflux; 2: diisopropylamine With sodium tetrahydroborate T=20°C;