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

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Reaction Steps

A solution of trans-{3-aminomethyl-1-[2-(4-fluorophenyl)-ethyl]-piperidin-4-yl}-benzyl-methylamine (96 mg, 270 μmol), [3-ethyl-5-(1-methyl-1H-tetrazol-5-yl)phenyl]-carbamic acid phenyl ester (87 mg, 270 μmol) and triethylamine (75 μL, 540 μmol) in N,N-dimethylformamide (2 mL) was stirred at room temperature for 20 hours. The solvent was removed under vacuum and the residue was dissolved in dichloromethane. The solution was washed with 1.0 N aqueous sodium hydroxide, then with water, and dried over sodium sulfate and concentrated under vacuum. The residue was purified by flash chromatography, eluting with 4% methanol in dichloromethane containing 0.4% (112 mg, 71%). 1H NMR (300 MHz, CDCl3) δ7.68 (s, 1H), 7.39 (m, 6H), 7.20 (s, 1H), 7.15 (m, 2H), 6.97 (t, J=9 Hz, 2H), 4.14 (s, 3H), 3.80 (m, 1H), 3.7-3.4 (m, 2H), 3.3-3.1 (m, 3H), 2.82 (m, 2H), 2.7-2.5 (m, 5H), 2.29 (s, 3H), 2.1-1.6 (m, 7H), 1.20 (t, J=7 Hz, 3H). Mass spec (ES+) m/z 585.6 (M+H+).

Provenance & Evidence