Hydrochloric Acid → (S)-1-(6-Fluoro-1-phenyl-1H-benzoimidazol-2-yl)ethylamine dihydrochloride

Participants

Reaction Conditions

Reaction Steps

[(S)-1-(4-Fluoro-2-phenylaminophenylcarbamoyl)ethyl]carbamic acid tert-butyl ester (40 g, 0.11 mol) was dissolved in HCl in dioxane (4N, 135 mL) and the reaction mixture heated at 60° C. for 3 h. The reaction mixture was cooled to RT and seeded with a crystal of the desired product causing the product to crystallise. The product was collected by filtration and dried in vacuo to give the title compound as a purple solid (31.2 g, 89%). 1H NMR 400 MHz (DMSO-d6) δ: 8.94 (3H, br s), 7.81 (1H, dd, J=8.8, 4.9 Hz), 7.74-7.62 (5H, m), 7.25-7.18 (1H, m), 6.98 (1H, dd, J=9.0, 2.4), 4.41 (1H, quintet, J=6.3 Hz), 1.45 (3H, d, J=6.4 Hz). LCMS: RT=2.02 min, [M+H]+=256 (10%) [M−NH2]=239 (100%).

Provenance & Evidence