p-Toluenesulfonic acid monohydrate → HCID 86656588, compound

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Reaction Steps

To a mixture of [4-(5-aminomethyl-2-fluoro-phenyl)-piperidin-1-yl]-[7-fluoro-1-(2-methoxy-ethyl)-4-trifluoromethoxy-1H-indol-3-yl]-methanone (488 mg, 0.95 mmol) in acetonitrile (3 mL) is added a solution of p-toluenesulfonic acid monohydrate (181 mg, 0.95 mmol) in acetonitrile (3 mL). This mixture is stored in a freezer overnight. The resulting beige crystal is collected by suction filtration, washed with toluene, and dried in vacuo at 50° C. overnight. The yield is 453 mg (69%). 1H NMR (DMSO-d6) δ 8.08 (bs, 3H), 7.70 (s, 1H), 7.80-6.95 (m, 9H), 5.00-4.30 (m, 3H), 4.20-3.90 (m, 2H), 3.80-3.60 (m, 3H), 3.23 (s, 3H), 3.25-2.80 (m, 3H), 2.28 (s, 3H), 1.95-1.45 (m, 4H); 19F NMR (DMSO-d6) δ −55.61 (s, 3F), −118.98 (s, 1F), −134.33 (d, J=9.3 Hz, 1F); LC 2.627 min; MS 512 (M+1, 100%). Mp 219° C. Infrared spectral features (cm−1): 1583, 1548, 1511, 1501, 1250, 1200, 1169, 1123, 1115.

Provenance & Evidence