Benzenemethanamine, 3-chloro- → 2-(3-Chloro-benzyl)-5-trifluoromethoxy-2,3-dihydro-isoindol-1-ylideneamine Hydrobromide

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Reaction Steps

To a solution of 3-chlorobenzylamine (62 mg, 0.442 mmol) in ethanol (500 μL) at 80° C. was added 2-bromomethyl-4-trifluoromethoxy-benzonitrile 16 (95 mg, 0.34 mmol) as a solution in ethanol (100 μL). After 30 min at 80° C., the ethanol was removed under reduced pressure, and the resulting residue was triturated with ether/ethanol to yield the title compound (colorless solid 90%). 1H NMR (400 MHz, CD3OD) δ8.48 (d, J=8.0 Hz, 1 H, Ar), 7.78 (s, 1 H, Ar), 7.71 (d, J=8.8 Hz, 1 H, Ar), 7.56 (s, 1 H, Ar), 7.45 (m, 2 H, Ar), 7.38 (m, 1 H, Ar), 5.12 (s, 2 H, CH2), 4.84 (s, 2 H, CH2); M/Z (ESI+) 341 ([M+H]+).

Provenance & Evidence