Hydrochloric Acid → HCID 13491595, compound

Participants

Reaction Steps

12.5 ml (0.131 mol) of 10.5N hydrochloric acid are added dropwise to a mixture of 26 g (0.1 mol) of 8-methyl-6-phenyl-6,7,8,9-tetrahydro-1H-pyrido[4,3-g]indole and 29.2 g (0.4 mol) of trimethylaminoborane in 150 ml of absolute dioxane at a temperature of 16° C., with stirring and in the absence of moisture. The mixture is then heated under reflux for 30 minutes and cooled to room temperature, 50 ml (0.3 mol) of 6N HCl are added and the mixture is heated under reflux once more for 15 minutes. After cooling to room temperature, 600 ml of H2O are added to the reaction mixture, the mixture is filtered over kieselguhr and, after addition of a further 600 ml of H2O, the filtrate is brought to pH 9 with 20% strength NaOH. The aqueous phase is now extracted several times with CH2Cl2 and, after drying over Na 2 SO4, the solvent is distilled off on a rotary evaporator. The oily residue is chromatographed on silica gel (silica gel 60 from E. Merck, Darmstadt) using ethyl acetate and MeOH (20:7) as the eluent.

Provenance & Evidence