Water → 3-[[5-(Trifluoromethyl)-2-pyridyl]oxy]-1-propanamine

Temperature

0 °C

2-Fluoro-5-trifluoromethylpyridine (1.831 g, 11 mmol) was dissolved in anhydrous THF (15 mL) with stirring under nitrogen and cooled to 0° C. in an ice bath. To this was added dropwise over 30 minutes a solution of 3-amino-1-propanol (0.76 mL, 10 mmol) in anhydrous THF (15 mL) and 1M potassium tert-butoxide in THF (10 mL, 10 mmol). The yellow solution was allowed to stir and slowly warm to room temperature overnight. The reaction mixture was poured into water (75 mL) and extracted with ether (2×50 mL). The organic phase was washed with brine (50 mL), dried (Na2SO4), filtered and evaporated under vacuum to a yellow liquid, which was nearly pure by NMR and MS, and was used as such without further purification.

1. stirringto stir
2. temperatureslowly warm to room temperature overnight
3. extractionextracted with ether (2×50 mL)
4. washThe organic phase was washed with brine (50 mL)
5. dry with materialdried (Na2SO4)
6. filtrationfiltered
7. customevaporated under vacuum to a yellow liquid, which
8. customsuch without further purification

ORD record

ord-d07a791be14640309bad24d49fc19a46

Source dataset

uspto-grants-2004_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06706740B2