Trifluoroacetic acid → 3-Bromo-5-(((4-phenylpiperidin-4-yl)methoxy)methyl)pyridine

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Reaction Steps

A solution of tert-butyl 4-(((5-bromopryidin-3-yl)methoxy)methyl)-4-phenylpiperidine-1-carboxylate (100 mg, 0.2 mmoL) in methylene chloride (2 mL) was treated with TFA (0.5 mL). After 1 h, the reaction was concentrated, and the resulting residue was evaporated from methylene chloride (2×). Preparative HPLC afforded 88.0 mg (92%) of the desired compound as its TFA salt. 1H-NMR (CDCl3, 400 MHz) δ 8.65 (s, 1H), 8.52 (s, 1H), 7.84 (s, 1H), 7.24-7.43 (m, 5H), 6.85 (s, br, 1H), 4.46 (s, 2H), 3.45 (s, 2H), 3.33-3.38 (m, 2H), 2.91-2.95 (m, 2H), 2.43-2.48 (m, 2H), 2.22-2.30 (m, 2H). Mass spec.: 362.99 (MH)+.

Provenance & Evidence