Sodium Cyanide → 2-Amino-2-(fluoromethyl)-5-methoxypentanenitrile

Temperature

-30 °C

Under an atmosphere of nitrogen, 3-methoxypropyl magnesium chloride is prepared from 3-methoxy-1-chloropropane (5.43 g, 50 mmol), prepared according to Haworth and Perkin, Chem. Zentralblatt, II, 1271 (1912) and magnesium turnings (1.22 g, 50 mmol) in dry THF (50 ml). The mixture is heated under reflux for 3 hours, then cooled to -30° C. and a solution of fluoroacetonitrile (2.95 g, 50 mmol) in THF (30 ml) is added during 20 minutes. After keeping the mixture at -30° C. for 1/2 hour more, a solution of sodium cyanide (4.9 g, 100 mmol) and ammonium chloride (8.09 g, 150 mmol) in water (100 ml), previously cooled to 0° C., is added and the mixture is stirred for 3/4 hour at room temperature. After saturating with sodium chloride, the THF layer is separated and the aqueous phase is extracted twice with ether. After drying (Na2SO4), the combined organic extracts are evaporated to give 2-fluoromethyl-2-amino-5-methoxypentanenitrile (4.0 g) as a brown oil.

1. customprepared
2. temperatureThe mixture is heated
3. temperatureunder reflux for 3 hours
4. customat -30° C.
5. customfor 1/2 hour
6. additionis added
7. concentrationAfter saturating with sodium chloride
8. customthe THF layer is separated
9. extractionthe aqueous phase is extracted twice with ether
10. dry with materialAfter drying (Na2SO4)
11. customthe combined organic extracts are evaporated

ORD record

ord-2b7703a477ff49669e7de67f7572a85c

Source dataset

uspto-grants-1988_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04743691