2-Bromotoluene → HCID 13041246, compound

Participants

Reaction Conditions

Reaction Steps

In a nitrogen atmosphere, 75 mL of 1.50 M n-butyllithium/hexane solution was dropwise added to tetrahydrofuran (100 mL) solution of 12 mL of 2-bromotoluene at −78° C., and stirred at −78° C. for 30 minutes. Tetrahydrofuran (50 mL) solution of 18.5 mL of 1-benzyl-4-piperidone was dropwise added to the reaction liquid, and stirred at room temperature for 4 hours. Aqueous saturated ammonium chloride solution and aqueous saturated sodium hydrogencarbonate solution were added in that order to the reaction liquid, extracted with ether, and the ether layer was washed with saturated saline water and dried with anhydrous sodium sulfate. The solvent was evaporated off under reduced pressure to obtain crude 1-benzyl-4-o-tolylpiperidin-4-ol as a yellow oily substance.

Provenance & Evidence