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-63c0cdaed38941f58fd169c42c84e20c

Source dataset

uspto-grants-2011_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07923461B2