ChemicalBook CAS DataBase List 2-(1H-Imidazol-1-yl)ethanamine

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

7synthesis methods

Product Name:2-(1H-Imidazol-1-yl)ethanamine
CAS Number:5739-10-6
Molecular formula:C5H9N3
Molecular Weight:111.15

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.

288-32-4 Synthesis

288-32-4
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870-24-6 Synthesis

870-24-6
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5739-10-6
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Yield:5739-10-6 34%

Reaction Conditions:

with sodium hydroxide;tetra(n-butyl)ammonium hydrogensulfate in acetonitrile; for 21 h;Heating / reflux;

Steps:

70.a

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)ethyl]amine as a pale yellow oil. ¹H NMR (DMSO-c/₆): 5 7.58 (s, 1H), 7.17 (s, 1H), 6.83 (s, 1H), 3.86 (t, 2H), 2.79 (t, 2H), 2.10 (brs, 2H).

References:

WO2006/20415,2006,A1 Location in patent:Page/Page column 154