Morpholine → 2-(4-Morpholinophenyl)ethanol

Participants

Reaction Conditions

Reaction Steps

A solution of 2-(4-bromophenethoxy)tetrahydro-2H-pyran (3.42 g, 12 mmol) in toluene (9.0 ml) and morpholine (1.22 g, 14 mmol) were added to a mixture of dry palladium acetate (32.3 mg, 0.14 mmol), 2-(di-t-butylphosphino)biphenyl (86.0 mg, 0.29 mmol) and sodium t-butoxide (1.73 g, 18 mmol), and they were stirred at 70° C. for 16 hours. Water was added to the reaction mixture. After the extraction with ethyl acetate, the product was extracted from the organic layer with 1 M hydrochloric acid. The aqueous layer was neutralized with an aqueous sodium hydroxide solution and the product was extracted with ethyl acetate. The organic layer was dried to obtain 4-morpholinophenethyl alcohol in the form of a light yellow solid (2.35 g, 95%).

Provenance & Evidence