Dimethylformamide → HCID 51703, compound

A mixture of 9.91 g of 3-(1,2,3,6-tetrahydropyridin-4-yl)-1H-indole, 10.6 g of sodium carbonate, 150 ml of dimethylformamide and 4.5 g of ethyl bromide was stirred under an inert atmosphere at 30°-35° C. for 5 hours and was then poured into 1.5 liters of water which caused precipitation. The mixture was stirred for one hour and filtered and the filter was rinsed with water. The recovered product was dried overnight in an oven at 70° C. under reduced pressure in the presence of dehydrating agent to obtain 8.95 g of raw product melting at 205° C. The product was dissolved in 400 ml of refluxing ethyl acetate and the mixture was filtered hot. The filtrate was concentrated to 250 ml and crystallization was effected for one hour. The mixture was filtered and the recovered product was rinsed with ethyl acetate to obtain 6.28 g of 3-(1-ethyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-indole in the form of yellow crystals melting at 205° C. Concentration of the mother liquors yielded another 1.76 g of product after crystallization for a total yield of 8.04 g.

1. customprecipitation
2. stirringThe mixture was stirred for one hour
3. filtrationfiltered
4. washthe filter was rinsed with water
5. customThe recovered product was dried overnight in an oven at 70° C. under reduced pressure in the presence
6. customto obtain 8.95 g of raw product melting at 205° C
7. filtrationthe mixture was filtered hot
8. concentrationThe filtrate was concentrated to 250 ml and crystallization
9. waitwas effected for one hour
10. filtrationThe mixture was filtered
11. washthe recovered product was rinsed with ethyl acetate

ORD record

ord-836d46ce5408479d91cb46bf24f186d0

Source dataset

uspto-grants-1981_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04278677