Hydrochloric Acid → HCID 22081320, compound

3 ml (23.2 mmol) of 5-bromo-2-methoxypyridine were added at −70° C. to a solution of 10.2 ml of butyllithium (2.5 M solution in hexane; 25.5 mmol) in 50 ml of diethyl ether. After 10 min, 1.4 ml (19.5 mmol) of propionitrile were added. After 2 hours at −70° C., the reaction mixture was slowly allowed to come to room temperature. 2.2 g of sodium sulfate decahydrate were then added and allowed to stir for 1 hour. After subsequent addition of 5 g of magnesium sulfate, the salts were filtered off after stirring briefly and the filtrate was concentrated. The residue was dissolved in 70 ml of methanol and 1.1 g (28 mmol) of sodium borohydride were added at 0° C. After stirring overnight, the reaction mixture was adjusted to pH 2 using concentrated hydrochloric acid and concentrated on a rotary evaporator. The residue was treated with 10 ml of water, and extracted once with diethyl ether. The aqueous phase was then saturated with sodium hydrogencarbonate, concentrated in vacuo and the residue was extracted with ethyl acetate. After drying and concentrating the ethyl acetate extracts, 1.4 g of racemic 1-(6-methoxypyridin-3-yl)propylamine were obtained.

1. waitAfter 2 hours at −70° C.
2. customto come to room temperature
3. filtrationthe salts were filtered off
4. stirringafter stirring briefly
5. concentrationthe filtrate was concentrated
6. dissolutionThe residue was dissolved in 70 ml of methanol
7. stirringAfter stirring overnight
8. concentrationconcentrated on a rotary evaporator
9. additionThe residue was treated with 10 ml of water
10. extractionextracted once with diethyl ether
11. concentrationsaturated with sodium hydrogencarbonate, concentrated in vacuo
12. extractionthe residue was extracted with ethyl acetate
13. customAfter drying
14. concentrationconcentrating the ethyl acetate

ORD record

ord-24919adb6e23499fa7910476c44d9e57

Source dataset

uspto-grants-2012_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08106099B2