sodium amide; 1,3-diamino-propane T=80°C; 5 h;

1: 90 percent / hydrogen / lindlar's catalyst / hexane; quinoline 2: 82 percent / PBr3, pyridine / diethyl ether / 1) rt, overnight, 2) reflux, 2 h 3: 1) Mg / 3) Li2CuCl4 / 1) THF, 2) THF, -10 deg C, 30 min, 3) a) 0 to -10 deg C, 6 h, b) rt, overnight 4: p-toluenesulphonic acid / methanol / 3 h / Heating 5: 68 percent / pyridine / 24 h / Ambient temperature View Scheme

1: 90 percent / hydrogen / lindlar's catalyst / hexane; quinoline 2: 82 percent / PBr3, pyridine / diethyl ether / 1) rt, overnight, 2) reflux, 2 h 3: 1) Mg / 3) Li2CuCl4 / 1) THF, 2) THF, -10 deg C, 30 min, 3) a) 0 to -10 deg C, 6 h, b) rt, overnight 4: p-toluenesulphonic acid / methanol / 3 h / Heating View Scheme

hydrogen; Lindlar's catalyst in quinoline; hexane

bis(cyclopentadienyl)titanium dichloride; lithium aluminium tetrahydride in tetrahydrofuran Heating;

1: 90 percent / H2, quinoline / Lindlar's catalyst / hexane 2: 80 percent / PBr3 / pyridine; diethyl ether / 2 h / Heating 3: 1.) Mg, 1,2-dibromoethane; 2.) Li2CuCl4 / 1.) THF; 2.) THF, -10 deg C, 4 h View Scheme