4-Vinylpyridine → 4-Pyridineethanamine

4-Vinylpyridine (5.26 ml, 50 mmol) and ammonium chloride (5.35 g, 100 mmol, 2.0 eq) were dissolved in methanol (2.5 ml) and water (15 ml), and the mixture was stirred with reflux for 23 hours. This reaction mixture was poured into ice water, and a 15% aqueous sodium hydroxide solution was added to make the same strong alkaline. The mixture was extracted 3 times with chloroform (50 ml). The organic layers were combined, washed with saturated brine and dried over anhydrous sodium sulfate. The drying agent was filtered off, and the filtrate was concentrated under reduced pressure. The obtained residue was distilled under reduced pressure to give 2-(4-pyridyl)ethylamine (1) (1.80 g, 30%; 87° C./6 mmHg) as a colorless oil. The residue from the distillation was subjected to column chromatography (chloroform/methanol=30/1-9/1) to give bis[2-(4-pyridyl)ethyl]amine (2) (1.11 g, 20%) as a pale-yellow oil.

1. temperaturewith reflux for 23 hours
2. extractionThe mixture was extracted 3 times with chloroform (50 ml)
3. washwashed with saturated brine
4. dry with materialdried over anhydrous sodium sulfate
5. filtrationThe drying agent was filtered off
6. concentrationthe filtrate was concentrated under reduced pressure
7. distillationThe obtained residue was distilled under reduced pressure

ORD record

ord-7f8abb63a936460aa4ca5a2a97349e84

Source dataset

uspto-grants-2000_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06017919