Multi-step reaction with 12 steps
1.1: toluene-4-sulfonic acid / acetone / 3 h / 20 °C
1.2: pH 7
2.1: sodium hydrogencarbonate / tetrahydrofuran / 15 h / 20 °C
3.1: triethylamine / dichloromethane / 1 h / 20 °C
4.1: methylamine / tetrahydrofuran / 6.5 h / 20 - 50 °C / Cooling with ice
5.1: N-ethyl-N,N-diisopropylamine; tetra-(n-butyl)ammonium iodide / acetonitrile / 4 h / 65 °C
6.1: cyclohexa-1,4-diene; ethanol / palladium 10% on activated carbon / 2 h / 85 °C / Reflux
7.1: triethylamine / butan-1-ol / 2 h / 150 °C / 12929 Torr / Microwave irradiations
8.1: acetic acid / 3.25 h / Reflux
9.1: ammonium hydroxide / dichloromethane; water / 3 h / 90 °C / Sealed tube
10.1: methylamine / methanol / 0.83 h / 20 - 65 °C
11.1: triethylamine / dichloromethane / 1 h / 20 °C
12.1: trifluoroacetic acid; water / 1.5 h / 20 °C / Cooling with ice
With
ammonium hydroxide; ethanol; cyclohexa-1,4-diene; water; tetra-(n-butyl)ammonium iodide; sodium hydrogencarbonate; toluene-4-sulfonic acid; acetic acid; triethylamine; N-ethyl-N,N-diisopropylamine; methylamine; trifluoroacetic acid;
palladium 10% on activated carbon;
In
tetrahydrofuran; methanol; dichloromethane; water; acetone; acetonitrile; butan-1-ol;