9-(((2-(Trifluoromethyl)phenyl)methyl)imino)-1,2,3,4,9,10-hexahydroacridin-1-ol → 1-Acridinol, 1,2,3,4-tetrahydro-6-fluoro-9-(((2-(trifluoromethyl)phenyl)methyl)amino)-

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Reaction Steps

To a cooled solution of 5.7 g of 3,4-dihydro-6-fluoro-9-(2-trifluoromethylbenzylamino)acridin-1(2H)-one in 80 ml of tetrahydrofuran was added 7.5 ml of 1 of molar solution of lithium aluminum hydride in THF. This was stirred for 0.5 hour and then quenched with 6 ml of saturated ammonium chloride solution. The inorganics were filtered, rinsed with ethyl acetate and the combined organics were dried over anhydrous magnesium sulfate. This was concentrated to a solid which was triturated with ether to give 5.1 g of a powder. This was twice recrystallized from ethyl acetate/hexane to give 3.1 g of analytically pure crystals, mp 149°-153° C.

Provenance & Evidence