[CH:1]1[C:13]2[NH:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.Br[CH2:15][CH2:16][CH2:17][CH:18]=[CH2:19].[Cl-].C([NH+](CC)CC)C.[OH-].[Na+]>O1CCCC1.O>[CH:15]([N:12]1[C:11]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=2[C:5]2[C:13]1=[CH:1][CH:2]=[CH:3][CH:4]=2)=[CH:16][CH2:17][CH2:18][CH3:19]Carbazole (30.1 g, 0.18 mol), 5-bromo-1-pentene (25.5 g, 0.17 mol), and triethylammonium chloride (6 g, 0.026 mol) were combined in tetrahydrofuran (200 mL), and a solution of sodium hydroxide (14 g, 0.35 mol) in water (60 mL) was added. The mixture was heated at reflux with stirring for 6 hours, then cooled to room temperature and left overnight. The aqueous layer was separated and the organic phase was concentrated to dryness. The crude product was redissolved in diethyl ether (100 mL) and washed with water (2×50 mL), dried (Na2SO4,) and then concentrated in vacuo. Recrystallization from methanol afforded N-pentenyl-carbazole as cream-colored needles (27.6 g, 65%), m.p.=47° C.
Loading…
