Multi-step reaction with 11 steps
1.1: potassium carbonate / acetone / 21 h / Inert atmosphere; Reflux
2.1: N,N-dimethyl-formamide / 8 h / 70 °C / Inert atmosphere
3.1: hydrazine hydrate / dichloromethane; methanol / 17 h / 20 °C
4.1: triethylamine / dichloromethane / 19 h / 20 °C / Inert atmosphere
5.1: hydrogen; palladium 10% on activated carbon / chloroform; ethyl acetate / 23 h / 20 °C
6.1: sodium hydride / N,N-dimethyl-formamide / 0.25 h / 0 °C / Inert atmosphere
6.2: 48 h / 20 °C / Inert atmosphere
7.1: hydrogen; palladium 10% on activated carbon / chloroform / 23 h / 20 °C
8.1: sodium hydride / N,N-dimethyl-formamide / 0.25 h / 0 °C / Inert atmosphere
8.2: 18 h / 20 °C / Inert atmosphere
9.1: trifluoroacetic acid / dichloromethane / 19 h / 20 °C
10.1: triethylamine / dichloromethane / 4 h / -10 - 20 °C / Inert atmosphere
11.1: sodium iodide / 1,4-dioxane / 48 h / Reflux
With
palladium 10% on activated carbon; hydrogen; sodium hydride; potassium carbonate; hydrazine hydrate; triethylamine; trifluoroacetic acid; sodium iodide;
In
1,4-dioxane; methanol; dichloromethane; chloroform; ethyl acetate; N,N-dimethyl-formamide; acetone;
3.1: |Gabriel Amine Synthesis;
DOI:10.1002/ejoc.201402249