HCID 16753850, compound → 1-[4-Fluoro-2-(methylsulfanyl)phenyl]methanamine

Temperature

25 °C

A slurry of 4-fluoro-2-(methylthio)benzamide (9 g, 48.6 mmol) in diethyl ether (500 mL) was cooled to zero degrees C. under nitrogen and lithium aluminum hydride (5.53 g, 145.8 mmol, 1.0 M in diethyl ether) was added dropwise. The reaction was allowed to stir with slow warming to 25 degrees C. overnight. The reaction was quenched via the addition of water (5.53 mL), 15% NaOH (5.53 μL) and water (16 mL). The mixture was stirred, the lithium salts precipitated out and were filtered off. The organic filtrate was washed with saturated sodium bicarbonate (300 mL) and brine (300 mL), dried over Na2SO4, filtered and reduced to a small volume. The resulting brown oil was placed under high vacuum to give the desired compound as a free base.

1. customovernight
2. customThe reaction was quenched via the addition of water (5.53 mL), 15% NaOH (5.53 μL) and water (16 mL)
3. stirringThe mixture was stirred
4. customthe lithium salts precipitated out and
5. filtrationwere filtered off
6. washThe organic filtrate was washed with saturated sodium bicarbonate (300 mL) and brine (300 mL)
7. dry with materialdried over Na2SO4
8. filtrationfiltered

ORD record

ord-3b50cac85b0a4aea96eebd444edd242f

Source dataset

uspto-grants-2005_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06921759B2