反应详情

A solution of 8.5 g. of 9-carbamoyl 9-(3-oxobutyl)fluorene from Example 2 in 400 ml of ethanol containing 5.0 g. of 5% polladium on carbon and 35 ml. of ethylamine was stirred at 150° C. for eight hours under 1000 psi of hydrogen. The reaction mixture was cooled, filtered and concentrated to dryness. The product was dissolved in 100 ml. of ethyl acetate and 100 ml. of diethyl ether and the solution was extracted several times with 6N hydrochloric acid. The acidic extracts were combined, cooled in an ice bath and made alkaline by addition of 10% sodium hydroxide. The alkaline solution was extracted with fresh ethyl acetate and diethyl ether. The organic layer was washed with water, dried and concentrated to dryness to provide 8.2 g. of the title product. The product was chromatographed over silica gel (eluting with 1% diethylamine in methanol v/v). The chromatographed product was dissolved in diethyl ether and the solution was stirred during addition of hydrogen chloride. The precipitated crystals were collected by filtration and recrystallized from ethanol and ethyl acetate to afford 5.1 g. of 9-carbamoyl-9-(3-ethylaminobutyl)fluorene hydrochloride. m.p. 180°-182° C.

1. temperatureThe reaction mixture was cooled
2. filtrationfiltered
3. concentrationconcentrated to dryness
4. dissolutionThe product was dissolved in 100 ml
5. extractionof diethyl ether and the solution was extracted several times with 6N hydrochloric acid
6. temperaturecooled in an ice bath
7. additionby addition of 10% sodium hydroxide
8. extractionThe alkaline solution was extracted with fresh ethyl acetate and diethyl ether
9. washThe organic layer was washed with water
10. customdried
11. concentrationconcentrated to dryness
12. customto provide 8.2 g