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

ORD record

ord-09b97f538d314d5bba05372458adca02

Source dataset

uspto-grants-1978_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04107313