Hydrochloric Acid → Mofegiline

Temperature

25 °C

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 (D2O, 300 MHz) δ 2.50 (m, 2H), 2.79 (m, 2H), 3.47 (d, J=3.0Hz, 2H), 6.80 (d, J=81.9Hz, 1H), 7.09 (m, 2H), 7.28 (m, 2H).

1. temperatureHeat to reflux
2. customSeparate the layers
3. distillationDistill the aqueous layer until the volume
4. temperatureCool to 50° C
5. additionAdd concentrated aqueous hydrochloric acid solution (50 g)
6. temperatureCool to -5° C.
7. filtrationfilter
8. washrinse with toluene
9. customdry in vacuo at 60° C.
10. customto give a solid
11. customRecrystallize the solid from isopropyl acetate
12. filtrationfilter
13. customdry in vacuo at 43° C.

ORD record

ord-898866fad8584ed4956fdb255999d01d

Source dataset

uspto-grants-1997_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05679854