Acetonitrile → 1-[2-[Bis(4-fluorophenyl)methoxy]ethyl]pyrrolidine

1-[Bis(4-fluorophenyl)methoxy]-2-chloroethane (3) (0.92 g, 3.3 mmol) was added to acetonitrile (50 ml) containing potassium carbonate (1.1 g, 8.0 mmol). This was followed by the addition of pyrrolidine (0.51 g, 7.2 mmol). The resulting mixture was then heated to reflux for 72 hours under an atmosphere of nitrogen. At the end of this time, the solution was added to ether (75 ml), washed with water (50 ml) and brine (50 ml). This was then dried over anhydrous magnesium sulfate, filtered and evaporated at reduced pressure to give a clear light yellow oil. The oil was chromatographed on silica gel and eluted with 3:1 ethyl acetate/methanol to afford the desired product (4) (500 mg, 48%) as a clear light yellow oil.

1. temperatureThe resulting mixture was then heated
2. temperatureto reflux for 72 hours under an atmosphere of nitrogen
3. washwashed with water (50 ml) and brine (50 ml)
4. dry with materialThis was then dried over anhydrous magnesium sulfate
5. filtrationfiltered
6. customevaporated at reduced pressure
7. customto give a clear light yellow oil
8. customThe oil was chromatographed on silica gel
9. washeluted with 3:1 ethyl acetate/methanol

ORD record

ord-e46e307586d74e3889ff99bf33479c04

Source dataset

uspto-grants-1998_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05747523