Hydrochloric Acid → 1-(2-(4-Methylpiperazin-1-yl)ethyl)-7-nitro-1,2,3,4-tetrahydroquinoline

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Reaction Conditions

Reaction Steps

Under a nitrogen atmosphere, 6 g (18 mmol) of 2-(4-methylpiperazin-1-yl)-1-(7-nitro-3,4-dihydroquinolin-1(2H)-yl)ethanone are dissolved in 20 ml of anhydrous THF. With stirring, at 0° C., a solution of 100 ml of 1.0M BH3 in THF (5.5 eq) is added. The temperature was allowed to return to ambient temperature and stirring was carried out for 24 h, before acidifying (drop by drop) with 1N HCl (considerable foaming and release of gas), and the medium was then brought to reflux for 0.5 h. After a return to ambient temperature, a 4.0N aqueous solution of NaOH was added. The medium was extracted several times with ethyl acetate. The combined organic phases were dried over Na2SO4, and then filtered. After removal of the solvent, a residue was obtained, which was purified on a silica column (dichloromethane-methanol). 1-(2-(4-Methylpiperazin-1-yl)ethyl)-7-nitro-1,2,3,4-tetrahydroquinoline was thus obtained in the form of an orange powder (Mp 58-60° C.).

Provenance & Evidence