1-Bromohexane → 4-Benzyl-2-(4-hexyloxy-phenyl)-morpholine

Participants

Reaction Steps

To a mixture of 4-(4-benzyl-morpholin-2-yl)-phenol (1.33 g; 4.94 mmol) in water (10 mL) and 1,4-dioxane (10 mL) was added KOH (0.55 g; 9.88 mmol), 1-bromohexane (1.04 mL; 7.41 mmol) and tetrabutylammonium bromide (0.16 g; 0.49 mmol), the resulting mixture was heated under reflux overnight. After cooling to RT the mixture was concentrated in vacuo, and partitioned between EtOAc and 5% aqueous NaHCO3solution. The organic layer was dried (Na2SO4), filtered, and concentrated in vacuo. The residue was purified by column chromatography (SiO2, Et2O: hexanes 1:1) to afford 4-benzyl-2-(4-hexyloxy-phenyl)-morpholine (1.31 g).

Provenance & Evidence