Hydrochloric Acid → Mofegiline

Participants

Reaction Conditions

Reaction Steps

Combine (E)-N-(2-(fluoromethylene)-4-(p-fluorophenyl)butyl)-N-formyl formamide (8.0 g, 32.7 mmol), ethanol (19.9 g), water (29.8 g), and aqueous 12M hydrochloric acid solution (13.1 g). Heat to reflux. After 1 hour, add toluene (29.8 g). Cool to 25° C. Separate the layers. Distill the aqueous layer until the volume is reduced by about two thirds. Cool to 50° C. Add concentrated aqueous hydrochloric acid solution (50 g). Cool to -5° C., filter , rinse with toluene, and dry in vacuo at 60° C. to give a solid. Recrystallize the solid from isopropyl acetate, filter, and dry in vacuo at 43° C. to give the title compound: mp 130°-131.5° C. 1H NMR (D20, 300 MHz) 8 2.50 (m, 2H), 2.79 (m, 2H), 3.47 (d, J=3.0 Hz, 2H), 6.80 (d, J=81.9 Hz, 1H), 7.09 (m, 2H), 7.28 (m, 2H).

Provenance & Evidence