Pyridine → N~1~,N~7~-Dipropylheptane-1,7-diamine

HRID 436660Notes

Reaction equation

HRID 436660 reaction equation
N1C=C[CH:4]=[CH:3][CH:2]=1.[C:7](Cl)(=O)[CH2:8][CH3:9].[CH2:12]([NH2:20])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][NH2:19].C(N)(=O)CCCCCCCCCCCC(N)=O>C1C=CC=CC=1>[CH2:7]([NH:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][NH:20][CH2:2][CH2:3][CH3:4])[CH2:8][CH3:9]

Participants

6

Reactant 4

HCID 1049PyridineHCID 62324Propionyl chlorideHCID 695331,7-HeptanediamineHCID 21387966Tridecanediamide

Product 1

HCID 15610182N~1~,N~7~-Dipropylheptane-1,7-diamine

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

The intermediate N,N'-di-n-propyl-1,7-heptanediamine was prepared as follows: To a solution containing 43.5 g. of pyridine in 600 ml. of benzene cooled in an ice bath was added dropwise over a period of 10 minutes 51.0 g. of propionyl chloride. To the resulting stirred and cooled solution was added dropwise over a period of 30 minutes 32.5 g. of 1,7-heptanediamine. After the ice bath was removed, the reaction mixture was stirred at room temperature for 20 hours and then filtered to remove a pale yellow solid. The filtrate was evaporated in vacuo. The residual material was combined with the pale yellow solid and the mixture was shaken well with a mixture of 500 ml. of chloroform, 500 ml. of water and 10 ml. of 12N hydrochloric acid. The layers were separated and the acidic aqueous layer was extracted with four 150 ml. portions of chloroform. The combined chloroform extracts were dried over anhydrous potassium carbonate. When the solid separated from the chloroform solution, an additional 750 ml. of chloroform was added. The mixture was heated to boiling and filtered through a sintered glass funnel. The chloroform solution was evaporated in vacuo and the solid residue was recrystallized from 250 ml. of acetonitrile and dried in a vacuum oven at 50° C. to yield 43.1 g. of heptamethylenebis(propionamide), m.p. 132°-133.5° C.

Workup

  1. additionTo a solution containing 43.5 g
  2. additionwas added dropwise over a period of 10 minutes 51.0 g
  3. temperaturecooled solution
  4. additionwas added dropwise over a period of 30 minutes 32.5 g
  5. customAfter the ice bath was removed
  6. stirringthe reaction mixture was stirred at room temperature for 20 hours
  7. filtrationfiltered
  8. customto remove a pale yellow solid
  9. customThe filtrate was evaporated in vacuo
  10. stirringthe mixture was shaken well with a mixture of 500 ml
  11. customThe layers were separated
  12. extractionthe acidic aqueous layer was extracted with four 150 ml
  13. dry with materialThe combined chloroform extracts were dried over anhydrous potassium carbonate
  14. customWhen the solid separated from the chloroform solution
  15. additionof chloroform was added
  16. temperatureThe mixture was heated
  17. filtrationfiltered through a sintered glass funnel
  18. customThe chloroform solution was evaporated in vacuo
  19. customthe solid residue was recrystallized from 250 ml
  20. dry with materialof acetonitrile and dried in a vacuum oven at 50° C.
  21. customto yield 43.1 g

Sources & evidence

ORD record
ord-b656dd4057d9472fbc21f6738269a92e
Source dataset
uspto-grants-1977_02
Patent number
US04009208

Reaction notes

Loading…