1,3-Propanediamine → N-(3-aminopropyl)pyridin-2-amine

A mixture of 2-bromopyridine (12.3 mL, 126.7 mmol) and pyridine (13 mL, 161 mmol) in 1,3-diaminopropane (53.5 mL, 640 mmol) was refluxed under nitrogen for 18 hours. The reaction mixture was evaporated under reduced pressure and cooled, and the resulting residue was treated with THF (150 mL) to yield a white precipitate. The precipitate was filtered and washed with additional THF (100 mL). Evaporation of the filtrate afforded an orange oil, which was distilled in vacuo to give N-(2-pyridinyl)-1,3-propanediamine (9.6 g, 50%) as a colorless oil: bp 128-132° C. (2 mmHg).

1. temperaturewas refluxed under nitrogen for 18 hours
2. customThe reaction mixture was evaporated under reduced pressure
3. temperaturecooled
4. additionthe resulting residue was treated with THF (150 mL)
5. customto yield a white precipitate
6. filtrationThe precipitate was filtered
7. washwashed with additional THF (100 mL)
8. customEvaporation of the filtrate
9. customafforded an orange oil, which
10. distillationwas distilled in vacuo

ORD record

ord-335483d1bcb24d6a831088e64c89838b

Source dataset

uspto-grants-2004_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06794385B2