Methanol → 2-[(9-Benzyl-6-methoxy-9H-carbazol-4-yl)oxy]ethylamine

Participants

Reaction Conditions

Reaction Steps

To a mixture of [(9-benzyl-6-methoxy-9H-carbazol-4-yl)oxy]acetonitrile (0.43 g, 1.26 mmol) in dry THF (20 mL) is added borane-methylsulfide complex (0.36 mL, 3.8 mmol). The mixture is heated at 85° C. overnight. Methanol is slowly added to the mixture until gas evolution ceased. The solvents are removed under reduced pressure. Methanol (20 mL) is added then removed under reduced pressure. Methanol (50 mL) and concentrated hydrochloric acid (10 mL) is added to the mixture and heated at 65° C. overnight. The mixture is neutralized with saturated potassium carbonate and partitioned between water and CH2Cl2. The layers are separated and the organic layer washed twice with water (100 mL). The CH2Cl2 is dried over anhydrous sodium sulfate and concentrated. Column chromatography with silica gel (60 mL) using 4% CH3OH in CH2Cl2 gave 0.371 g (85%) of the title compound; IR (drift) 1581, 1488, 1467, 1452, 1440, 1343, 1323, 1289, 1271, 1211, 1167, 1150, 1031, 742, 727 cm−1. HRMS (FAB) calcd for C22H22N2O2+H1 347.1759, found 347.1761. % Water (KF): 0.17. 1H NMR (CDCl3) δ3.28, 3.92, 4.28, 5.47, 6.65, 6.95, 7.02, 7.09, 7.21, 7.32, 7.87; Anal. Calcd for C22H22N2O2: C, 76.15; H, 6.41; N, 8.07. Found: C, 75.90; H, 6.38; N, 7.99.

Provenance & Evidence