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

Temperature

200 °C

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.

1. temperaturewas then cooled
2. stirringThe mixture was stirred until dissolution
3. extractionThe mixture was extracted with methylene chloride
4. washthe organic phase was washed with aqueous saturated sodium chloride solution
5. customdried
6. customevaporated to dryness under reduced pressure
7. customThe residue was chromatographed over silica gel
8. washwas eluted with a 95-5 chloroform-methanol mixture
9. distillationThe solution was distilled to dryness under reduced pressure
10. filtrationThe solution was filtered
11. customevaporated to dryness under reduced pressure

ORD record

ord-c8590540d6144047b4399c9456d47a0c

Source dataset

uspto-grants-1983_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04382942