Ethanolamine → 2-[(2-Hydroxyethyl)amino]-N-3-pyridinylacetamide

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Reaction Steps

Chloroacetyl chloride (2.2 mL, 27.6 mmol) was added dropwise over 10 minutes to a stirred, cooled (0° C.) solution of 3-pyridinamine (2 g, 21 mmol) and triethylamine (4 mL, 28 mmol) in tetrahydrofuran (30 mL). The mixture was allowed to warm to room temperature, then 2-aminoethanol (5 mL, 120 mmol) in methanol (5 mL) was added. The mixture was stirred at 60° C. for 4 hours, cooled and the solvent was evaporated under reduced pressure. The residue was purified by flash column chromatography on silica gel, eluting with CH2Cl2/MeOH/NH3(Aq.) (90:10:1), to give the title compound (2.53 g, 62%). m/z (ES+) 196 (M+1).

Provenance & Evidence