1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine in dichloromethane T=20°C; 12 h;

1.1: potassium hydroxide / dimethyl sulfoxide / 1 h / 50 °C 1.2: 50 °C 2.1: water; potassium hydroxide / dimethyl sulfoxide / 80 - 85 °C 2.2: 50 - 60 °C 3.1: N-chloro-succinimide / N,N-dimethyl-formamide / 18 h / 22 °C 4.1: oxalyl dichloride; N,N-dimethyl-formamide / toluene / 1 h / 45 °C 5.1: N-ethyl-N,N-diisopropylamine / dichloromethane / Large scale reaction 5.2: 0 °C / Large scale reaction 6.1: hydrazine hydrate / ethanol; tert-butyl methyl ether / 16 h / 40 °C 6.2: 40 °C 7.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / dichloromethane / 12 h / 20 °C View Scheme

1.1: ethyl acetate / 1.5 h 2.1: di-isopropyl azodicarboxylate; triphenylphosphine / methanol; toluene / 42 - 60 °C 2.2: 2 h / 60 °C 3.1: AlCl3, aluminium chloride / 22 h / -5 °C 3.2: 35 - 50 °C 3.3: 18 h / 65 °C 4.1: N-ethyl-N,N-diisopropylamine / acetonitrile / 5 - 8 °C 5.1: tetrabutylammomium bromide; sodium hydrogencarbonate / acetonitrile / 26 h / Reflux; Large scale reaction 6.1: hydrazine hydrate / ethanol; tert-butyl methyl ether / 16 h / 40 °C 6.2: 40 °C 7.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / dichloromethane / 12 h / 20 °C View Scheme

1.1: N-chloro-succinimide / N,N-dimethyl-formamide / 18 h / 22 °C 2.1: oxalyl dichloride; N,N-dimethyl-formamide / toluene / 1 h / 45 °C 3.1: N-ethyl-N,N-diisopropylamine / dichloromethane / Large scale reaction 3.2: 0 °C / Large scale reaction 4.1: hydrazine hydrate / ethanol; tert-butyl methyl ether / 16 h / 40 °C 4.2: 40 °C 5.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / dichloromethane / 12 h / 20 °C View Scheme

1.1: water; potassium hydroxide / dimethyl sulfoxide / 80 - 85 °C 1.2: 50 - 60 °C 2.1: N-chloro-succinimide / N,N-dimethyl-formamide / 18 h / 22 °C 3.1: oxalyl dichloride; N,N-dimethyl-formamide / toluene / 1 h / 45 °C 4.1: N-ethyl-N,N-diisopropylamine / dichloromethane / Large scale reaction 4.2: 0 °C / Large scale reaction 5.1: hydrazine hydrate / ethanol; tert-butyl methyl ether / 16 h / 40 °C 5.2: 40 °C 6.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / dichloromethane / 12 h / 20 °C View Scheme

1.1: oxalyl dichloride; N,N-dimethyl-formamide / toluene / 1 h / 45 °C 2.1: N-ethyl-N,N-diisopropylamine / dichloromethane / Large scale reaction 2.2: 0 °C / Large scale reaction 3.1: hydrazine hydrate / ethanol; tert-butyl methyl ether / 16 h / 40 °C 3.2: 40 °C 4.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / dichloromethane / 12 h / 20 °C View Scheme

1.1: di-isopropyl azodicarboxylate; triphenylphosphine / methanol; toluene / 42 - 60 °C 1.2: 2 h / 60 °C 2.1: AlCl3, aluminium chloride / 22 h / -5 °C 2.2: 35 - 50 °C 2.3: 18 h / 65 °C 3.1: N-ethyl-N,N-diisopropylamine / acetonitrile / 5 - 8 °C 4.1: tetrabutylammomium bromide; sodium hydrogencarbonate / acetonitrile / 26 h / Reflux; Large scale reaction 5.1: hydrazine hydrate / ethanol; tert-butyl methyl ether / 16 h / 40 °C 5.2: 40 °C 6.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / dichloromethane / 12 h / 20 °C View Scheme

1.1: N-ethyl-N,N-diisopropylamine / dichloromethane / Large scale reaction 1.2: 0 °C / Large scale reaction 2.1: hydrazine hydrate / ethanol; tert-butyl methyl ether / 16 h / 40 °C 2.2: 40 °C 3.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / dichloromethane / 12 h / 20 °C View Scheme

1.1: di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 0 - 20 °C / Large scale reaction 2.1: bis-triphenylphosphine-palladium(II) chloride / 1,4-dioxane / 5 h / Reflux; Large scale reaction 3.1: N-bromosuccinmide / tetrahydrofuran; water / 0 - 10 °C / Large scale reaction 4.1: sodium hydrogencarbonate / acetonitrile / 3 h / Reflux; Large scale reaction 5.1: hydrogenchloride / 1,4-dioxane / 2 h / 25 °C / Large scale reaction 6.1: N-ethyl-N,N-diisopropylamine / dichloromethane / Large scale reaction 6.2: 0 °C / Large scale reaction 7.1: hydrazine hydrate / ethanol; tert-butyl methyl ether / 16 h / 40 °C 7.2: 40 °C 8.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / dichloromethane / 12 h / 20 °C View Scheme

1.1: N-bromosuccinmide / tetrahydrofuran; water / 0 - 10 °C / Large scale reaction 2.1: sodium hydrogencarbonate / acetonitrile / 3 h / Reflux; Large scale reaction 3.1: hydrogenchloride / 1,4-dioxane / 2 h / 25 °C / Large scale reaction 4.1: N-ethyl-N,N-diisopropylamine / dichloromethane / Large scale reaction 4.2: 0 °C / Large scale reaction 5.1: hydrazine hydrate / ethanol; tert-butyl methyl ether / 16 h / 40 °C 5.2: 40 °C 6.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / dichloromethane / 12 h / 20 °C View Scheme