Sodium Iodide → HCID 9821567, compound

Participants

Reaction Steps

9-Benzyl-6-methyl-9H-carbazol-4-ol (0.0597 g, 0.21 mmol), 2-diethylaminoethylchloride hydrochloride (0.0565 g, 0.33 mmol), potassium carbonate (0.1007 g, 0.73 mmol), sodium iodide (0.0054 g, 0.036 mmol) and DMF (1 mL) are heated at 85° C. for 4.5 h. After the mixture had cooled, it is partitioned between water and ether. The aqueous layer is also washed twice with ethyl acetate. The combined organic layers are dried over magnesium sulfate and concentrated to dryness. The residue is chromatographed on silica gel (60 mL) using methanol/dichloromethane (1/99 to 3/97 to 5/95) to give 0.0605 g (75%) of the title compound containing N-{2-[(9-benzyl-3-bromo-6-methyl-9H-carbazol-4-yl)oxy]ethyl}-N,N-diethylamine as an impurity. Attempts at purifying this material through recrystallization are unsuccessfull; MS (ESI+) for C26H30N2O m/z 387.3 (M+H)+. 1H NMR (CDCl3) δ1.17 2.53, 2.78, 3.17, 4.37, 5.47, 6.68, 6.96, 7.11, 7.21-7.34, 8.17.

Provenance & Evidence