Hydrochloric Acid → 2-(4-Ethylpiperidin-1-yl)ethanamine hydrochloride

The title compound was prepared according to general procedure H described in Scheme 3. The crude triethylsilane solution of 2-(4-ethylpiperidin-1-yl)acetonitrile was added carefully to a slurry of LiAlH4 (8.3 equiv., 1.2 g, 31 mmol) in ether (5 mL) and stirred at RT under Ar for 14 h. The crude reaction mixture containing a white precipitate was cooled to 0° C. and treated dropwise with 10% aqueous NaOH (1 mL) and stirred for 30 min. The cooled mixture was treated with H2O (2.1 mL) to provide a thick precipitate. The mixture was then treated with ether (10 mL), stirred and filtered. The filter cake was washed with ether (5×10 mL). The combined ether layer was concentrated under reduced pressure to provide a concentrated solution in ether/H2O that was acidified to pH 2 with 1 N HCl. The mixture was concentrated under reduced pressure to provide 2-(4-ethylpiperidin-1-yl)ethanamine hydrochloride as a brown oil (200 mg, 28% yield).

1. customThe title compound was prepared
2. customThe crude reaction mixture
3. additioncontaining a white precipitate
4. temperaturewas cooled to 0° C.
5. stirringstirred for 30 min
6. customto provide a thick precipitate
7. stirringstirred
8. filtrationfiltered
9. washThe filter cake was washed with ether (5×10 mL)
10. concentrationThe combined ether layer was concentrated under reduced pressure
11. customto provide a concentrated solution in ether/H2O that
12. concentrationThe mixture was concentrated under reduced pressure

ORD record

ord-affb92bb2d234991afccf52243fb05b5

Source dataset

uspto-grants-2012_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08114894B2