Hydrochloric Acid → 2,6,N'-trimethyl-N'-(4-trifluoromethyl-benzyl)-benzene-1,4-diamine

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Reaction Conditions

Reaction Steps

Concentrated aqueous hydrochloric acid (2 mL) was added to N-{2,6-dimethyl-4-[methyl-(4-trifluoromethyl-benzyl)-amino]-phenyl}-acetamide (0.20 g) and heated to 130° C. for 80 minutes in a sealed microwave process vial. The crude mixture was poured onto solid potassium hydroxide (2 g) mixed with ice. The product was extracted with 1,2-dichloroethane (100 mL), and the organic phase was filtered through solid sodium carbonate (5 g), dried over magnesium sulfate and concentrated in vacuo to furnish 0.10 g (57% yield) of the title compound as a pale brown oil. LC-MS (m/z) 309 (MH+); tR=2.11, (UV, ELSD) 99%, 98%. 1H NMR (500 MHz, DMSO-d6): 2.03 (s, 6H), 2.76 (s, 3H), 3.94 (b, 2H), 4.41 (s, 2H), 6.39 (s, 2H), 7.42 (d, 2H), 7.65 (d, 2H).

Provenance & Evidence