p-Toluenesulfonic acid monohydrate → HCID 86635740, compound

Participants

Reaction Conditions

Reaction Steps

Add a solution of 1-Methyl-1-(6-trifluoromethyl-pyridin-3-yl)-ethylamine (280 g, 1.37 moles) in methyl t-butyl ether (1.4 L) to a solution of p-toluenesulfonic acid monohydrate (212.5 g, 1.23 moles) in tetrahydrofuran (980 mL). Observe a pH of 2.0 and an exotherm to 28° C. Cool to 18° C. and filter solids. Rinse filter cake with methyl t-butyl ether (1.4 L). Vacuum dry the filter cake at ambient temperature and collect 408 g (79%) of the titled compound as a white solid. 1H NMR (DMSO-d6, 500 MHz): δ 8.94 (d, 1H, J=2.5), 8.53 (br s, 3H), 8.2 (dd, 1H, J=5.5, 8), 8.02 (d, 1H, J=8), 7.46 (d, 2H, J=8), 7.10 (d, 2H, J=7.5), 2.27 (s, 3H), 1.68 (s, 6H).

Provenance & Evidence