Sodium Chloride → HCID 21453009, compound

The intermediate N,N'-diethyl-trans-3-heptene-1,7-diamine was prepared in two steps as follows: To 100 ml. of pyridine cooled to 0° C. (in an ice-salt bath) was added dropwise with stirring 35.8 g. of acetic anhydride. To the cooled stirred solution was added 18 g. of trans-3-heptene-1,7-diamine in 40 ml. of pyridine at such a rate to keep the temperature less than 10° C.; the addition took about 45 minutes. The reaction mixture was stirred at 5°-10° C. for an additional 30 minutes, was next stirred at room temperature for 6 hours and then allowed to stand at 5° C. overnight. The clear solution was treated with 10 ml. of concentrated ammonium hydroxide with cooling and stirring. The solution was distilled under reduced pressure to remove most of the volatile materials to leave a clear viscous oil. The oil was treated with 100 ml. of water followed by the addition of solid sodium chloride. The mixture was extracted with five 50 ml. portions of chloroform. The combined chloroform extracts were shaken with 100 ml. of saturated brine containing 2 ml. of 6N hydrochloric acid and then dried over anhydrous potassium carbonate. The chloroform was distilled off in vacuo to yield a clear viscous oil which crystallized at room temperature. The solid was purified by dissolving it in chloroform-methanol, treating the solution with decolorizing charcoal and removing the solvents in vacuo to yield, as a clear colorless viscous oil which crystallized at room temperature to yield 28.3 g. of N,N'-(trans-3-heptene-1,7-diyl)bis(acetamide).

1. additionwas added dropwise
2. stirringTo the cooled stirred solution
3. additionwas added 18 g
4. customthe temperature less than 10° C.
5. additionthe addition
6. stirringThe reaction mixture was stirred at 5°-10° C. for an additional 30 minutes
7. stirringwas next stirred at room temperature for 6 hours
8. waitto stand at 5° C. overnight
9. additionThe clear solution was treated with 10 ml
10. stirringstirring
11. distillationThe solution was distilled under reduced pressure
12. customto remove most of the volatile materials
13. customto leave a clear viscous oil
14. additionThe oil was treated with 100 ml
15. extractionThe mixture was extracted with five 50 ml
16. stirringThe combined chloroform extracts were shaken with 100 ml
17. dry with materialof 6N hydrochloric acid and then dried over anhydrous potassium carbonate
18. distillationThe chloroform was distilled off in vacuo
19. customto yield a clear viscous oil which
20. customcrystallized at room temperature
21. customThe solid was purified
22. dissolutionby dissolving it in chloroform-methanol
23. additiontreating the solution with decolorizing charcoal
24. customremoving the solvents in vacuo
25. customto yield, as a clear colorless viscous oil which
26. customcrystallized at room temperature
27. customto yield 28.3 g

ORD record

ord-d75eb5435eaa4c7a9a3c7558a453dc7a

Source dataset

uspto-grants-1977_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04009208