Ethylenediamine → 6-[(2-Aminoethyl)amino]pyridine-3-carbonitrile

Temperatur

77.5 °C

A mixture of 2-chloro-5-cyanopyridine (0.60 M) in acetonitrile (120 ml) and ethylene diamine (85 ml) were stirred overnight (ca. 16 h) at 75-80° C. under argon. The ethylene diamine was removed under reduced pressure and then dried in vacuo for 2-3 h. The residual solution was basified with 1 M sodium hydroxide solution (˜100 ml). The aqueous solution was saturated with sodium chloride and extracted with a solution of 95% ethyl acetate and 5% methanol (3×150 ml) and with a solution of 95% acetonitrile and 5% methanol (3×150 ml). The organic extracts were combined and extracted with a saturated sodium chloride solution (2×70 ml). The organic layer was dried with sodium sulfate, filtered, and concentrated under reduced pressure. The crude white to tan solid was triturated with ether (2×50 ml) and dried overnight in vacuo resulting in 78% yield of 6-[(2-aminoethyl)amino]pyridine-3-carbonitrile.

1. customThe ethylene diamine was removed under reduced pressure
2. customdried in vacuo for 2-3 h
3. extractionextracted with a solution of 95% ethyl acetate and 5% methanol (3×150 ml) and with a solution of 95% acetonitrile and 5% methanol (3×150 ml)
4. extractionextracted with a saturated sodium chloride solution (2×70 ml)
5. dry with materialThe organic layer was dried with sodium sulfate
6. filtrationfiltered
7. concentrationconcentrated under reduced pressure
8. customThe crude white to tan solid was triturated with ether (2×50 ml)
9. customdried overnight in vacuo

ORD-Eintrag

ord-75ea0628dfc5434fb8ce103e8be9f53e

Quelldatensatz

uspto-grants-2008_09

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07425557B2