反应详情

温度

100 °C

A mixture of 500 g. of 9-aminocarbonyl-9-(2-cyanoethyl)fluorene, 1500 ml. of isopropylamine and 100 g. of 5% palladium on carbon was placed in a one gallon high pressure hydrogenation bomb. The bomb was pressurized with hydrogen to a pressure of 1500 psi, and the reaction mixture was then stirred at 100° C. for ten hours, and for an additional eight hours at room temperature. The reaction mixture was filtered to remove the hydrogenation catalyst, and the solvent was removed from the filtrate by evaporation under reduced pressure. The residue was dissolved in ethyl acetate, and the solution was extracted several times with 1N hydrochloric acid. The acidic extracts were combined, made alkaline by the addition of sodium hydroxide, and the alkaline mixture was extracted with fresh ethyl acetate. The organic layer was separated, washed with water and dried. Removal of the solvent by evaporation under reduced pressure provided 9-(3-isopropylaminopropyl)-9-aminocarbonylfluorene as a solid residue. The solid was dissolved in methanol and treated with anhydrous hydrogen chloride. The crystalline product which formed was recrystallized from chloroform to afford 391 g. of 9-(3-isopropylaminopropyl)-9-aminocarbonylfluorene hydrochloride. Yield 60%. m.p. 216.5°-217° C.

1. additionA mixture of 500 g
2. filtrationThe reaction mixture was filtered
3. customto remove the hydrogenation catalyst
4. customthe solvent was removed from the filtrate by evaporation under reduced pressure
5. dissolutionThe residue was dissolved in ethyl acetate
6. extractionthe solution was extracted several times with 1N hydrochloric acid
7. additionby the addition of sodium hydroxide
8. extractionthe alkaline mixture was extracted with fresh ethyl acetate
9. customThe organic layer was separated
10. washwashed with water
11. customdried
12. customRemoval of the solvent
13. customby evaporation under reduced pressure