1: 90 percent / NaNH2, H2N(CH2)3NH2 / 2.5 h / 80 °C 2: 94 percent / H2 / Pd-CaCO3 / methanol / 0.75 h 3: 80 percent / Pd(OAc)2, PPh3, NaHCO3 / dimethylformamide / 12 h / 120 °C 4: H2 / Pd-C / methanol / 2 h View Scheme

sodium amide; 1,3-diamino-propane T=80°C; 2.5 h;

1: 90 percent / NaNH2, H2N(CH2)3NH2 / 2.5 h / 80 °C 2: 94 percent / H2 / Pd-CaCO3 / methanol / 0.75 h View Scheme

1: 72.1 percent / NaNH2, 1,3-diaminopropane / 4 h / 80 °C 2: 85 percent / PTSA / CH2Cl2 / 8 h / Ambient temperature 3: 1.) LiNH2, liq. NH3, HMPA / 1.) -33 deg C, 2 h, 2.) THF, -33 deg C, 6 h 4: 90 percent / PTSA / methanol; H2O / 12 h / Ambient temperature 5: 88.8 percent / DMAP / pyridine / 8 h / Ambient temperature 6: 85 percent / H2, quinoline / Lindlar catalyst / ethanol View Scheme

1: 72.1 percent / NaNH2, 1,3-diaminopropane / 4 h / 80 °C 2: 85 percent / PTSA / CH2Cl2 / 8 h / Ambient temperature 3: 1.) LiNH2, liq. NH3, HMPA / 1.) -33 deg C, 2 h, 2.) THF, -33 deg C, 6 h 4: 90 percent / PTSA / methanol; H2O / 12 h / Ambient temperature 5: 78 percent / Na, liq. NH3 / 2 h 6: 90 percent / DMAP / pyridine / 8 h / Ambient temperature View Scheme

1: 72.1 percent / NaNH2, 1,3-diaminopropane / 4 h / 80 °C 2: 85 percent / PTSA / CH2Cl2 / 8 h / Ambient temperature 3: 1.) LiNH2, liq. NH3, HMPA / 1.) -33 deg C, 2 h, 2.) THF, -33 deg C, 6 h View Scheme

1: 72.1 percent / NaNH2, 1,3-diaminopropane / 4 h / 80 °C 2: 85 percent / PTSA / CH2Cl2 / 8 h / Ambient temperature 3: 1.) LiNH2, liq. NH3, HMPA / 1.) -33 deg C, 2 h, 2.) THF, -33 deg C, 6 h 4: 90 percent / PTSA / methanol; H2O / 12 h / Ambient temperature View Scheme

1: 72.1 percent / NaNH2, 1,3-diaminopropane / 4 h / 80 °C 2: 85 percent / PTSA / CH2Cl2 / 8 h / Ambient temperature 3: 1.) LiNH2, liq. NH3, HMPA / 1.) -33 deg C, 2 h, 2.) THF, -33 deg C, 6 h 4: 90 percent / PTSA / methanol; H2O / 12 h / Ambient temperature 5: 78 percent / Na, liq. NH3 / 2 h View Scheme

hydrogen; Lindlar's catalyst; Pb-poisoned Pd