Triethylamine → 1-[3-Ethyl-5-(1-methyl-1H-tetrazol-5-yl)phenyl]-3-{trans-1-[2-(4-fluorophenyl)-ethyl]-4-methylpiperidin-3-ylmethyl}-urea

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A solution of trans-1-[2-(4-fluorophenyl)ethyl]-4-methyl-piperidin-3-ylmethylamine (12 mg, 46 μmol) and [3-ethyl-5-(1-methyl-1H-tetrazol-5-yl)phenyl]-carbamic acid phenyl ester (15 mg, 46 μmol) in N,N-dimethylformamide (0.5 mL) was treated with triethylamine (13 μL, 93 μmol). After 23 hours, the mixture was concentrated under vacuum. The residue was purified by flash chromatography, eluting with 3% methanol in dichloromethane containing 0.3% aqueous ammonium hydroxide, provided an amorphous solid (19 mg, 86%). 1H NMR (300 MHz, CDCl3) δ7.71 (s, 1H), 7.64 (s, 1H), 7.11 (m, 3H), 6.91 (t, J=9 Hz, 2H), 4.17 (s, 3H), 3.6-3.3 (m, 3H), 3.2-2.9 (m, 6H), 2.66 (q, J=7 Hz, 2H), 2.50 (m, 1H), 1.9-1.7 (m, 3H), 1.42 (m, 1H), 1.24 (t, J=7 Hz, 3H), 1.01 (d, J=7 Hz, 3H). Mass spec (ES+) m/z 480.4 (M+H+, 100%).

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