1-Benzyl-4-piperidone → HCID 68967526, compound

Participants

Reaction Steps

Magnesium (3.10 g, 127 mmol), iodine (135 mg, 0.531 mmol), and 2-(4-bromophenyl)-4,5-dihydro-4,4-dimethyloxazole (27 g, 106 mmol) were added to tetrahydrofuran (120 mL), and the mixture was heated under reflux for 1 hour. This reaction mixture was cooled to mom temperature, then 1-benzyl-4-piperidone (21.7 mL, 117 mmol) was added, and the mixture was heated under reflux for 3 hours. The reaction mixture was cooled to room temperature and then a saturated aqueous ammonium chloride solution and ethyl acetate were added for partition. The aqueous layer was extracted with ethyl acetate, and then the organic layers were combined and washed serially with water and a saturated saline solution. The organic layer was dried over anhydrous magnesium sulfate and filtered. The solvent was evaporated under vacuum and the resultant residue was purified with silica gel column chromatography (n-heptane:ethyl acetate=3:1-1:1). The target fraction was concentrated under vacuum to obtain the title compound (13.4 g, 35%).

Provenance & Evidence