Triethylamine → HCID 18545197, compound

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Reaction Steps

Racemic 3-(4-Chloro-phenyl)-8-aza-bicyclo[3.2.1]oct-2-ene (1.0 g, 4.55 mmol), triethylamine (0.70 mL, 5.01 mmol), and methanesulfonic acid 3-(2,2,2-trifluoro-acetylamino)-propyl ester (1.13 g, 4.55 mmol) in ethanol (20 mL) were refluxed for 15 hours. The mix was concentrated, diluted with saturated sodium bicarbonate (200 mL) and extracted with ethyl acetate (3×150 mL). Combined organic layers were washed with brine (200 mL), dried with magnesium sulfate and concentrated to a light brown oil. Silica gel flash chromatography using 5% methanol/chloroform as the eluent yielded racemic N-{3-[3-(4-Chloro-phenyl)-8-aza-bicyclo[3.2.1]oct-2-en-8-yl]-propyl}-2,2,2-trifluoro-acetamide (0.79 g, 46.5%) as a light brown oil which had the following properties: 1H NMR CDCl3 δ: 10.00 (brd s, 1H), 7.27 (s, 4H), 6.23 (d, J=5.4 Hz, 1H), 3.69-3.43 (m, 4H), 2.82-2.71 (m, 3H), 2.19-1.88 (m, 4H), 1.77-1.57 (m, 3H). IR (CHCl3): 3157, 2949, 2880, 1714, 1544, 1494, 1466, 1446, 1403, 1377, 1346, 1315, 1245, 1162, 1094, 1012, 973, 937, 817, (cm−1). Analysis calculated for C18H20ClF3N2O.3/4 H2O: C, 55.96; H, 5.61; N, 7.25; Found: C, 55.80; H, 5.09; N, 7.33.

Provenance & Evidence