Hydrochloric Acid → HCID 68669747, compound

Participants

Reaction Steps

A mixture of compound 4a as obtained from the above Synthesis Ex. 1 (1.26 g, 5 mmol) and 1-(2-aminoethyl)piperazine (1.94 g, 15 mmol) in 2-ethoxyethanol (50 mL) was heated at 140-150° C. for 48 hrs (by TLC monitoring). After cooling, the reaction mixture was evaporated in vacuo to give a residue, which was dissolved in ethyl acetate (EA) (50 mL). The EA layer was washed with H2O and brine, and then dried on MgSO4. Concentration of the EA layer gave a residue, which was dissolved in MeOH (10 mL), followed by addition of a solution of 6N HCl at 0° C. The resultant mixture was stirred at room temperature for 8 hrs to result in precipitation, followed by filtration. The precipitate thus collected was washed with MeOH and then dried at 90° C. under reduced pressure for 24 hrs to give N-(11H-indolo[3,2-c]quinolin-6-yl)-2-(piperazin-1-yl)ethanamine hydrochloride, which was purified by flash column chromatography (FCC) (silica gel; MeOH/CH2Cl2=1/10 to 1/3) to give the title compound 5 as an orange color powder (0.51 g, 29% yield).

Provenance & Evidence