Isopropylamine → 9-Carbamoyl-9-(3-isopropylaminopentyl)fluorene

Beteiligte Stoffe

Reaktionsschritte

A mixture of 14.6 g. of 9-carbamoyl-9-(3-oxopentyl)fluorene from Example 7 and 14.8 g. of isopropylamine in 100 ml. of methanol containing 3.7 g. of 5% palladium on charcoal was heated at 80° C. for eight hours at 750 psi hydrogen. The reaction mixture was cooled, filtered and concentrated to a volume of about 25 ml. The product was added to ethyl acetate and diethyl ether. The organic solution was extracted with 6N hydrochloric acid. The acidic extracts were combined, cooled in ice and made alkaline by addition of 10% sodium hydroxide. The alkaline solution was extracted several times with 50% ethyl acetate in diethyl ether. The extracts were combined, washed with water, dried and concentrated to dryness to provide 4.0 g. of the title compound. The product was dissolved in 50 ml. of ethyl acetate and stirred while 1.38 g. of maleic acid were added. The precipitated solid was collected by filtration and dried to afford 4.0 g. of 9-carbamoyl-9-(3-isopropylaminopentyl)fluorene maleate. m.p. 161°-163° C.

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