Ammonia → 3-(4-(4-Fluorophenoxy)phenyl)propanimidamide

To a solution of 3-(4-(4-fluorophenoxy)phenyl)propanenitrile (4.4 g, 18.24 mmol) in toluene (25 mL) and methanol (5.94 mL) was added dropwise AcCl (6.48 mL, 91 mmol) at 0° C. in 5 min. The mixture was stirred at room temperature for 2 h. The mixture was cooled to 0° C. in an ice bath, and ammonia (26.1 mL, 182 mmol) in methanol was added dropwise in 5 min. The mixture was stirred at room temperature overnight. The mixture was filtered to remove the solid, and the solid was washed with toluene (40 mL) and methanol (40 mL). The combined filtrate was concentrated in vacuo, the residue was triturated with diethyl ether, the resulting white solid was collected by filtration, washed with diethyl ether and dried in vacuo to afford the title compound (5.4 g, 16.12 mmol, 88% yield) as white solid. LCMS: rt=1.03 min, [M+H+]=259

1. temperatureThe mixture was cooled to 0° C. in an ice bath
2. stirringThe mixture was stirred at room temperature overnight
3. filtrationThe mixture was filtered
4. customto remove the solid
5. washthe solid was washed with toluene (40 mL) and methanol (40 mL)
6. concentrationThe combined filtrate was concentrated in vacuo
7. customthe residue was triturated with diethyl ether
8. filtrationthe resulting white solid was collected by filtration
9. washwashed with diethyl ether
10. customdried in vacuo

ORD record

ord-189687b2de8742b0a7b91fc6191e7db1

Source dataset

uspto-grants-2014_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08637536B2