1: 1,3-diamino-propane With sodium hydride in mineral oil T=70°C; 1 h; Inert atmosphere; 2: 5-docosyn-1-ol in mineral oil T=70°C; 18 h; Inert atmosphere;

1.1: N,N-dimethyl-formamide; anhydrous xylene / 0 - 20 °C / |Inert atmosphere 2.1: n-butyllithium / hexane; tetrahydrofuran / 10 h / 0 °C / |Inert atmosphere; |Reflux 2.2: 24 h / |Reflux; |Inert atmosphere 3.1: toluene-4-sulfonic acid / methanol / 18 h / 20 °C / |Inert atmosphere 4.1: sodium hydride / mineral oil / 1 h / 70 °C / |Inert atmosphere 4.2: 18 h / 70 °C / |Inert atmosphere View Scheme

1.1: n-butyllithium / hexane; tetrahydrofuran / 10 h / 0 °C / |Inert atmosphere; |Reflux 1.2: 24 h / |Reflux; |Inert atmosphere 2.1: toluene-4-sulfonic acid / methanol / 18 h / 20 °C / |Inert atmosphere 3.1: sodium hydride / mineral oil / 1 h / 70 °C / |Inert atmosphere 3.2: 18 h / 70 °C / |Inert atmosphere View Scheme

1.1: toluene-4-sulfonic acid / methanol / 18 h / 20 °C / |Inert atmosphere 2.1: sodium hydride / mineral oil / 1 h / 70 °C / |Inert atmosphere 2.2: 18 h / 70 °C / |Inert atmosphere View Scheme

potassium hydride; 1,3-diamino-propane