2-(1H-Imidazol-1-yl)ethanamine

The Uses of 2-(1H-Imidazol-1-yl)ethanamine

2-(1H-Imidazol-1-yl)ethanamine is an intermediate for the preparation of selective tumor inhibitor bis(nitroimidazolyl)alkanecarboxamide hypoxia.

Synthesis

Imidazole (8.10 g, 119 mmol), 2-chloroethylamine monohydrochloride (15.2 g, 131 mmol), tetrabutylammonium hydrogensulfate (1.62 g, 4.8 mmol), and sodium hydroxide (17.1 g, 428 mmol) were combined with 100 ml acetonitrile and heated under reflux for 21 h. The reaction mixture was cooled and filtered. The filtrate was concentrated to a pale yellow oil. Flash chromatography (silica gel, gradient elution of acetonitrile to 9:1 acetonitrile/NH4OH) afforded 4.52 g (34%) of 2-(1H-Imidazol-1-yl)ethanamine as a pale yellow oil.