Ethanolamine → 2-Phenoxyethanamine

Participants

Reaction Steps

Add sodium hydride (60% in mineral oil, 6.63 g, 166 mmol) to a solution of 2-hydroxyethylamine (10.0 mL, 166 mmol) in dioxane (150 mL) at room temperature under nitrogen. After stirring for 10 minutes at room temperature, add 2-chloropyridine (15.6 mL, 166 mmol) and heat the reaction mixture to reflux. After stirring at reflux for 14 hours, cool the reaction mixture to room temperature and dilute with water (100 mL) and methylene chloride (200 mL). Extract the aqueous layer with methylene chloride (2×100 mL). Wash the combined organic phase with brine (200 mL), dry over magnesium sulfate, filter, and concentrate to an orange oil. Flash chromatography on silica gel eluting with 50% of a (80:18:2 CHCl3/MeOH/concentrated NH4OH) solution in methylene chloride affords 2-phenoxy-ethylamine as a yellow oil (17.9 g, 78%). 1H NMR (CDCl3) δ 8.09-8.15 (m, 1H), 7.53-7.56 (m, 1H), 6.80-6.85 (m, 1H), 6.70-6.75 (m, 1H), 4.27-4.31 (m, 2H), 3.06-3.10 (m, 2H); MS (ES): m/z 139 (M+H).

Provenance & Evidence