O-Xylene → 1-Benzyl-3-(3-methoxyphenyl)-1,2,5,6-tetrahydropyridine

Participants

Reaction Conditions

Reaction Steps

A mixture of 3.25 g of the product of Step A and 65 ml of xylene was heated to 140° C. with stirring and after the addition of 2 g of phosphoric acid anhydride, the mixture was stirred at 140° C. for 2 hours and was then iced. Ice was then added to the mixture with caution and was diluted with water and ethyl acetate. The mixture was made alkaline by addition of triethylamine and was stirred until total dissolution occurred. The mixture was filtered and the decanted aqueous phase was extracted with ethyl acetate. The organic extract was washed with aqueous saturated sodium chloride solution, dried and evaporated to dryness under reduced pressure. The residue was chromatographed over silica gel and was eluted with a 9-1 cyclohexane-ethyl acetate mixture to obtain 1.97 g of 1-benzyl-3-(3-methoxyphenyl)-1,2,5,6-tetrahydropyridine.

Provenance & Evidence