Sodium Hydroxide → HCID 13408438, compound

Temperature

215 °C

Alternatively, 4-(heptylamino)pyridine was prepared as follows: A mixture containing 229 g. (1.0 mole) of N-(4-pyridyl)pyridinium chloride hydrochloride and 228 g. (1.5 moles) of n-heptylamine hydrochloride was heated 2 hours with stirring in an oil bath at a bath temperature of 215° C. The reaction mixture was cooled to 80° C., diluted with ice-water, made alkaline with 35% aqueous sodium hydroxide and extracted successively with ether and chloroform. The organic extracts were combined and evaporated to dryness under reduced pressure. The residual viscous oil was dissolved in ether and the ethereal solution was washed with water. The aqueous wash was back-extracted with chloroform and the chloroform extracts were combined with the ethereal solution. The combined organic solutions were dried over anhydrous sodium sulfate and evaporated to dryness under reduced pressure. Cooling the residual oil to -78° C. effected partial solidification. The semi-solid was diluted with a small amount of ether and filtered. The solid so-obtained was dissolved in a mixture of acetonitrile and chloroform, the resulting solution treated with decolorizing carbon, filtered, and the filtrate evaporated to dryness under reduced pressure. The resulting semi-solid was diluted with a small amount of ether and cooled. The solid thus-produced was collected by filtration and washed with a small volume of cold ether to give, after drying, 84.6 g. of 4-(heptylamino)pyridine, m.p. 50°-52° C.

1. additionA mixture containing 229 g
2. temperatureThe reaction mixture was cooled to 80° C.
3. extractionextracted successively with ether and chloroform
4. customevaporated to dryness under reduced pressure
5. dissolutionThe residual viscous oil was dissolved in ether
6. washthe ethereal solution was washed with water
7. washThe aqueous wash
8. extractionwas back-extracted with chloroform
9. dry with materialThe combined organic solutions were dried over anhydrous sodium sulfate
10. customevaporated to dryness under reduced pressure
11. temperatureCooling the residual oil to -78° C.
12. additionThe semi-solid was diluted with a small amount of ether
13. filtrationfiltered
14. customThe solid so-obtained
15. additionthe resulting solution treated with decolorizing carbon
16. filtrationfiltered
17. customthe filtrate evaporated to dryness under reduced pressure
18. additionThe resulting semi-solid was diluted with a small amount of ether
19. temperaturecooled
20. customThe solid thus-produced
21. filtrationwas collected by filtration
22. washwashed with a small volume of cold ether
23. customto give
24. customafter drying

ORD record

ord-25330d80fc8a43b4bb0c5e4242c7977f

Source dataset

uspto-grants-1980_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04206215