Potassium Carbonate → HCID 9820840, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 9-benzyl-9H-Carbazol-4-ol (0.0305 g, 0.1116 mmol), potassium carbonate (0.0308 g, 0.2232 mmol), and DMF (1.0 mL) is stirred at 100° C. Diethylaminoethyl chloride hydrochloride (0.0230 g, 0.1339 mmol) is added in aliquots over 40 min. After 2.3 h, an additional 0.032 g of potassium carbonate and 0.023 g of diethylaminoethyl chloride hydrochloride are added. The mixture is stirred overnight and then the solvent is removed and the residue partitioned between CH2Cl2 and aq. sodium bicarbonate. The organic layers are dried over sodium sulfate. Chromatography on silica gel (15 mL) using acetone-hexane (20/80) gave 0.0382 g of the title compound as a solid; mp 79-80.5° C.; IR (drift) 2965, 1581, 1457, 1439, 1356, 1342, 1333, 1268, 1147, 1112, 1053, 782, 750, 729, 713 cm−1; 1H NMR (CDCl3) δ1.14, 2.75, 3.13, 4.36, 5.50, 6.71, 6.98, 7.12, 7.2-7.4, 8.38. Anal. Calcd for C25H28N2O: C, 80.61; H, 7.58; N, 7.52. Found: C, 79.90; H, 7.52; N, 7.43.

Provenance & Evidence