1-Propanol, 3-(dibutylamino)- → Bis(3-dibutylaminopropyl)fluoranthene-3,8-dicarboxylate dihydrochloride

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Reaction Steps

To 700 ml of chloroform is added 10.0 g (0.033 mole) of fluoranthene-3,8-dicarbonyl chloride and 12.4 g (0.066 mole) of 3-dibutylaminopropanol and the resulting solution is refluxed overnight. Upon cooling a solid forms which is crystallized from chloroform-ethyl acetate and twice from methanol-ethyl acetate. Further purification is achieved by dissolving the solid in water with subsequent conversion of the solid to the free base by the action of cold 3 N. aqueous potassium hydroxide, extraction of the free base with ether and after drying the ether solution converting the basic ester to the dihydrochloride salt with ethereal-hydrogen chloride. The product is crystallized from methanol-butanone-ether to give bis(3-dibutylaminopropyl)fluoranthene-3,8-dicarboxylate dihydrochloride hemidrate. M.P. 169°-173°C.

Provenance & Evidence