Hydrochloric Acid → (4,5-Dihydro-oxazol-2-yl)-{4-[1-(4-fluoro-phenyl)-1H-indol-5-yloxy]-butyl}-methyl-amine

Participants

Reaction Steps

300 mg (0.96 mmol) {4-[1-(4-Fluoro-phenyl)-1H-indol-5-yloxy]-butyl}-methylamine in 10 ml THF were treated with 150 mg (1.4 mmol) 2-chloroethylisocyanate and the mixture stirred at room temperature during 10 hours. After addition of 0.2 ml NEt3 the mixture was stirred for an additional hour and treated with 0.1 M aqueous HCl. Extraction with Et2O, drying of the combined organic layers with Na2SO4, Evaporation of the solvent, and column chromatography on silica gel with CH2Cl2/MeOH/NEt3 10:1:0.1 gave 60 mg (16%) (4,5-Dihydro-oxazol-2-yl)-{4-[1-(4-fluoro-phenyl)-1H-indol-5-yloxy]-butyl}-methyl-amine, MS: 382 (MH+).

Provenance & Evidence