Grubb's 2nd generation catalyst; toluene-4-sulfonic acid in dichloromethane T=20°C; 18 h; Inert atmosphere;

iron sulphate heptahydrate in methanol T=10°C; 3 h;

hydrogenchloride; potassium hydroxide; potassium carbonate 1.) THF, hexane, water, 15-20 min, room temp., 2.) water, pH 10-12; Yield given. Multistep reaction;

1: benzene / 16 h / Heating 2: 2.4 M n-BuLi, diisopropylamine / tetrahydrofuran; hexane / -78 - -45 °C 3: 1.) 10percent aq. HCl, 2.) K2CO3, 40percent aq. KOH / 1.) THF, hexane, water, 15-20 min, room temp., 2.) water, pH 10-12 View Scheme

1: 2.4 M n-BuLi, diisopropylamine / tetrahydrofuran; hexane / -78 - -45 °C 2: 1.) 10percent aq. HCl, 2.) K2CO3, 40percent aq. KOH / 1.) THF, hexane, water, 15-20 min, room temp., 2.) water, pH 10-12 View Scheme

1.1: toluene / 45 h / Reflux; Inert atmosphere 2.1: zinc / tetrahydrofuran / 20 °C / Inert atmosphere 3.1: 1,3-diamino-propane / 1 h / Reflux; Inert atmosphere 4.1: potassium hydroxide / N,N-dimethyl-formamide / 0.25 h / Inert atmosphere 4.2: 0.25 h / 20 °C / Inert atmosphere 5.1: Grubb's 2nd generation catalyst; toluene-4-sulfonic acid / dichloromethane / 18 h / 20 °C / Inert atmosphere View Scheme

1.1: zinc / tetrahydrofuran / 20 °C / Inert atmosphere 2.1: 1,3-diamino-propane / 1 h / Reflux; Inert atmosphere 3.1: potassium hydroxide / N,N-dimethyl-formamide / 0.25 h / Inert atmosphere 3.2: 0.25 h / 20 °C / Inert atmosphere 4.1: Grubb's 2nd generation catalyst; toluene-4-sulfonic acid / dichloromethane / 18 h / 20 °C / Inert atmosphere View Scheme

1.1: 1,3-diamino-propane / 1 h / Reflux; Inert atmosphere 2.1: potassium hydroxide / N,N-dimethyl-formamide / 0.25 h / Inert atmosphere 2.2: 0.25 h / 20 °C / Inert atmosphere 3.1: Grubb's 2nd generation catalyst; toluene-4-sulfonic acid / dichloromethane / 18 h / 20 °C / Inert atmosphere View Scheme

palladium

palladium 10 on activated carbon; hydrogen in methanol T=20°C; P=760.051 Torr; 3 h;