Pyridine → N'-ethylheptane-1,7-diamine

The intermediate N-ethyl-1,7-heptanediamine was prepared in two steps as follows: To a stirred mixture kept in an ice bath and containing 7.2 g. of pyridine, 100 ml. of benzene and 9.2 g. of acetic anhydride was added dropwise over a period of a few minutes 10.0 g. of 7-aminoheptanonitrile. The ice bath was removed and the mixture was stirred at room temperature overnight. The reaction mixture was then evaporated to dryness and the residue taken up in a mixture of 60 ml. of water and 60 ml. of chloroform. The mixture was acidified with 6N hydrochloric acid and shaken well. The layers were separated and the aqueous layer was extracted with four 60 ml. portions of chloroform. The combined extracts were dried over anhydrous potassium carbonate and the solvent removed in vacuo to yield, as a viscous yellow liquid, 15.1 g. of 7-acetamidoheptanonitrile.

1. customTo a stirred mixture kept in an ice bath
2. additioncontaining 7.2 g
3. customThe ice bath was removed
4. customThe reaction mixture was then evaporated to dryness
5. additionthe residue taken up in a mixture of 60 ml
6. stirringshaken well
7. customThe layers were separated
8. extractionthe aqueous layer was extracted with four 60 ml
9. dry with materialThe combined extracts were dried over anhydrous potassium carbonate
10. customthe solvent removed in vacuo
11. customto yield, as a viscous yellow liquid, 15.1 g

ORD record

ord-2b1889b44908454c855eaed74f010be1

Source dataset

uspto-grants-1977_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04009208