Ethylenediamine → N1-(pyridin-4-yl)ethane-1,2-diamine

Ethylenediamine (10.4 ml, 155 mmol) was added to 4-bromopyridine hydrochloride (3.00 g, 15.5 mmol) under a nitrogen atmosphere, and the mixture was refluxed for 1.5 hours. The temperature was cooled to room temperature, potassium carbonate (8.57 g, 62.0 mmol) was added to the reaction mixture, and the whole was stirred for 10 minutes. Then, the solid was filtered out and washed with toluene and 2-propanol successively. The filtrate was concentrated under reduced pressure, the residue was purified by basic silica gel column chromatography, and the resulting solid was filtered off with diisopropyl ether to give 1.63 g (77%) of the titled compound as a pale yellow solid.

1. temperaturethe mixture was refluxed for 1.5 hours
2. filtrationThen, the solid was filtered out
3. washwashed with toluene and 2-propanol successively
4. concentrationThe filtrate was concentrated under reduced pressure
5. customthe residue was purified by basic silica gel column chromatography
6. filtrationthe resulting solid was filtered off with diisopropyl ether

ORD record

ord-058da2b8cb024016b60ad8909917c9ed

Source dataset

uspto-grants-2006_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07098226B2