Dimethylamine → HCID 58993667, compound

Participants

Reaction Steps

A stirred solution of 3-bromo-5-(((1-(tert-butoxycarbonyl)-4-phenylpiperidin-4-yl)methoxy)methyl)benzoic acid (160 mg, 0.32 mmol) in dimethylformamide (5 mL) was cooled to 0° C. and sequentially treated with methylene chloride (2 mL), dimethylamine (1 N in tetrahydrofuran, 0.32 mL, 0.32 mmol), N,N-diisopropylethylamine (90 μL, 0.64 mmol), and PyBop® (0.21 g, 0.38 mmol). The solution was stirred for 1.5 h and concentrated. The product was purified by column chromatography (30% ethyl acetate/hexanes) to give 120 mg (70%). 1H-NMR (CDCl3, 500 MHz) δ 7.38-7.40 (m, 1H), 7.33-7.35 (m, 4H), 7.22-7.24 (m, 2H), 7.03 (s, 1H), 4.32 (s, 2H), 3.74-3.77 (m, 2H), 3.38 (s, 2H), 3.08 (s, 3H), 2.99-3.05 (m, 2H), 2.90 (s, 3H), 2.16-2.19 (m, 2H), 1.83-1.89 (m, 2H), 1.43 (s, 9H). Mass spec.: 533.24 (MH)+.

Provenance & Evidence