Isopropyl iodide → HCID 3055752, compound

Temperature

50 °C

3.15 g of silver oxide and 2.25 ml of isopropyl iodide were added to a solution of 4.5 g of 3-(1,2,3,6-tetrahydropyridin-4-yl)-1H-indole in 90 ml of acetone and the mixture was heated at 50° C. for 3 hours and was then cooled. The mixture was filtered and the filtrate was distilled to dryness under reduced pressure. The residue was chromatographed over silica gel and was eluted with a 6-3-1 chloroform-acetone-triethylamine mixture. The fractions were distilled to dryness and the residue was dissoved in 200 ml of refluxing ethyl acetate. The mixture was filtered and the filtrate was concentrated to 150 ml and cooled to 20° C. Crystallization was induced and the mixture was iced overnight and vacuum filtered. The recovered product was washed with ethyl acetate and dried to obtain 3.9 g of 3-(1-propyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-indole melting at 210° C.

1. temperaturewas then cooled
2. filtrationThe mixture was filtered
3. distillationthe filtrate was distilled to dryness under reduced pressure
4. customThe residue was chromatographed over silica gel
5. washwas eluted with a 6-3-1 chloroform-acetone-triethylamine mixture
6. distillationThe fractions were distilled to dryness
7. filtrationThe mixture was filtered
8. concentrationthe filtrate was concentrated to 150 ml
9. temperaturecooled to 20° C
10. customCrystallization
11. filtrationvacuum filtered
12. washThe recovered product was washed with ethyl acetate
13. customdried

ORD record

ord-5e072d81faa545eb9efdd6fb1017947e

Source dataset

uspto-grants-1981_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04278677