Aluminium lithium hydride → HCID 25160586, compound

Participants

Reaction Steps

Lithium aluminum hydride (1M in tetrahydrofuran, 1.07 ml, 1.07 mmol) was added to a solution of tert-butyl 4-(((1-methyl-5-(trifluoromethyl)-1H-indol-7-yl)methoxy)methyl)-4-phenylpiperidine-1-carboxylate (60 mg, 0.119 mmol) in tetrahydrofuran (5 ml). The reaction was heated at reflux for 3 h. The reaction was quenched by sequential dropwise addition of water (0.2 mL), 1N sodium hydroxide (0.6 mL), and more water (0.2 mL). The mixture was filtered and the filtrate evaporated. The residue was purified by chromatography on silica gel with a gradient from 5% to 10% 2M ammonia in methanol/dichloromethane. The product 1-methyl-7-(((1-methyl-4-phenylpiperidin-4-yl)methoxy)methyl)-5-(trifluoromethyl)-1H-indole (45 mg, 0.108 mmol, 91% yield) was isolated as a clear oil. 1H-NMR (CDCl3, 400 MHz) δ 7.82 (s, 1H), 7.22-7.36 (m, 6H), 6.93 (s, 1H), 6.49 (s, 1H), 4.65 (s, 2H), 3.63 (s, 3H), 3.42 (s, 2H), 2.53 (m, 2H), 2.20 (s, 3H), 2.13-2.25 (m, 4H), 1.94 (m, 2H); Mass spec. (MH)+: 417.13.

Provenance & Evidence