Ammonium Hydroxide → 3-(1-Propyl-1,2,5,6-tetrahydropyridin-3-yl)-phenol

Participants

Reaction Conditions

Reaction Steps

A mixture of 3.9 g of the product of Step A and 7.8 g of pyridinium hydrobromide was stirred under an inert atmosphere for 2 hours at 200° C. and was then cooled and taken up in water. The mixture was stirred until dissolution and was made alkaline by addition of ammonium hydroxide. The mixture was extracted with methylene chloride and the organic phase 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 95-5 chloroform-methanol mixture. The solution was distilled to dryness under reduced pressure and the residue was taken up in methylene chloride. The solution was filtered and evaporated to dryness under reduced pressure to obtain 3.13 g of 3-(1-propyl-1,2,5,6-tetrahydropyridin-3-yl)-phenol.

Provenance & Evidence