Aluminium lithium hydride → HCID 25160587, compound

Participants

Reaction Steps

Lithium aluminum hydride (1M in tetrahydrofuran, 1.71 ml, 1.71 mmol) was added to a solution of tert-butyl 4-phenyl-4-(((5-(trifluoromethyl)-1H-indol-7-yl)methoxy)methyl)piperidine-1-carboxylate (93 mg, 0.19 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 chromatographed on silica gel with 15% methanol in dichloromethane. The product 7-(((1-methyl-4-phenylpiperidin-4-yl)methoxy)methyl)-5-(trifluoromethyl)-1H-indole (52 mg, 0.129 mmol, 67.9% yield) was isolated as a clear oil. 1H-NMR (CDCl3, 400 MHz) δ 7.92 (bs, 1H), 7.78 (s, 1H), 7.32-7.48 (m, 5H), 7.08 (s, 1H), 6.85 (s, 1H), 6.45 (s, 1H), 4.72 (s, 2H), 3.52 (s, 2H), 2.73 (m, 2H), 2.31 (s, 3H), 2.22-2.40 (m, 4H), 2.12 (m, 2H); Mass spec. (MH)+: 403.11.

Provenance & Evidence