Fumaric Acid → HCID 131728949, compound

Participants

Reaction Steps

To a solution of 8-methoxy-2-methyl-5-phenyl-2,3,4,5-tetrahydro-1H-benzo[c]azepine from step B (260 mg, 0.97 mmol) in ethanol (4 mL) was added fumaric acid (123 mg, 0.97 mmol) in methanol (2 mL). The solvent was removed under reduced pressure. The residue was triturated with ethyl acetate and diethyl ether. The resulting precipitate was collected by filtration, washed with diethyl ether, and dried at 50° C. under vacuum to provide (+/−)-8-methoxy-2-methyl-5-phenyl-2,3,4,5-tetrahydro-1H-benzo[c]azepine, fumarate salt (250 mg, 67%, >99% AUC HPLC) as an off-white solid: mp 171-173° C.; 1H NMR (CD3OD, 500 MHz) δ 7.38 (t, J=7.5 Hz, 2H), 7.29 (t, J=7.4 Hz, 1H), 7.18 (d, J=7.5 Hz, 2H), 7.02 (d, J=2.7 Hz, 1H), 6.86-6.78 (m, 2H), 6.67 (s, 2H), 4.50 (dd, J=8.9, 1.9 Hz, 2H), 4.25 (d, J=13.9 Hz, 1H), 3.80 (s, 3H), 3.52-3.51 (m, 2H), 2.85 (s, 3H), 2.57-2.56 (m, 1H), 2.40-2.36 (m, 1H); ESI MS m/z=268 [C18H21NO+H]+.

Provenance & Evidence