Hydrogen Bromide → 1-Benzyl-4-(6-hydroxynaphth-2-yl)-1,2,3,6-tetrahydropyridine

Participants

Reaction Steps

A solution of 1.0 gm (2.9 mMol) 1-benzyl-4-hydroxy-4-(6-methoxynaphth-2-yl)piperidine and 0.65 mL (5.8 mMol) 48% hydrobromic acid in 10 mL acetic acid was heated at reflux for 18 hours. The reaction mixture was cooled to room temperature, neutralized with 5N sodium hydroxide, and extracted well with ethyl acetate. The organic extracts were combined, washed with saturated aqueous sodium chloride, dried over sodium sulfate, and concentrated under reduced pressure. The residual solid was suspended in a mixture of ethyl acetate and hexane and the suspension sonicated. The suspension was then filtered to provide 0.57 gm (63%) of the desired compound as a grey solid.

Provenance & Evidence