1: diethyl-(5-methoxy-1H-indol-3-ylmethyl)-amine With methyl iodide in tetrahydrofuran T=0 - 20°C; 24 h; 2: potassium cyanide in tetrahydrofuran 2 h; Heating; Further stages.;

in tetrahydrofuran; water Substitution; MeI adding to a pre-cooled indole (5 deg C) in THF; stirring overnight; aq. KCN adding; stirring at reflux under Ar;

1: 90 percent / tetrahydrofuran; H2O / MeI adding to a pre-cooled indole (5 deg C) in THF; stirring overnight; aq. KCN adding; stirring at reflux under Ar 2: 77 percent / Na / 2.5 h / 90 - 105 °C / Na adding insmall portions to a soln. of the indole in (EtO)2CO at 90 deg C; stirring 2 h at 105 deg C; evapg. 3: 91 percent / H2 / Raney-Ni W-2 / 8 h / 21 °C / 2585.74 Torr / in the excess of Ac2O 4: 88 percent / aq. NaOH / 8 h / refluxing under Ar; diluting with H2O; acidifying with AcOH up to pH 6.12; ppt. collecting by vacuum filtration 5: 77 percent / SOCl2; HCl / methanol; dioxane / 18 h / -10 - 21 °C / SOCl2 adding to a pre-cooled susp. of the acid in MeOH, stirring under Ar, evapg., treated with aq. K2CO3 and with 4 N HCl View Scheme