Allylamine → HCID 20337901, compound

HRID 1395666Notes

Reaction equation

HRID 1395666 reaction equation
[C:1]([NH:4][C:5]1[CH:6]=[CH:7][C:8]2[O:13][CH2:12][CH:11]([C:14]([O:16]CC)=O)[O:10][C:9]=2[CH:19]=1)(=[O:3])[CH3:2].[CH2:20]([NH2:23])[CH:21]=[CH2:22]>C(O)C>[C:1]([NH:4][C:5]1[CH:6]=[CH:7][C:8]2[O:13][CH2:12][CH:11]([C:14]([NH:23][CH2:20][CH:21]=[CH2:22])=[O:16])[O:10][C:9]=2[CH:19]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 7853AllylamineHCID 20337903HCID 20337903, compound

Product 1

HCID 20337901HCID 20337901, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A mixture of 3.5 g of 4A, 30 ml of 2-propenylamine and 25 ml of ethanol was stirred for 18 hours. The volatile materials were evaporated under reduced pressure and the residue was co-evaporated with ethanol until a solid formed. The solid was dissolved in a minimum amount of hot ethanol. The solution was filtered through charcoal, chilled and the solid product was separated. The solvent was evaporated under reduced pressure. The residue was held in a freezer over a weekend. 20 ml of water was added with stirring and the solid was collected. The solid was stirred with a further 20 ml of water; the solid was collected, washed with ether, and triturated with hexane until a gum precipitated. The solvent phase was separated. The gum was again triturated with hexane and the solvent phase was separated. The two extracts were combined; the solvent was evaporated under reduced pressure, and the residue was washed with ether, then dried to 4, as a solid, mp: 138°-140° C.

Workup

  1. customThe volatile materials were evaporated under reduced pressure
  2. customformed
  3. filtrationThe solution was filtered through charcoal
  4. temperaturechilled
  5. customthe solid product was separated
  6. customThe solvent was evaporated under reduced pressure
  7. waitThe residue was held in a freezer over a weekend
  8. addition20 ml of water was added
  9. stirringwith stirring
  10. customthe solid was collected
  11. stirringThe solid was stirred with a further 20 ml of water
  12. customthe solid was collected
  13. washwashed with ether
  14. customtriturated with hexane until a gum
  15. customprecipitated
  16. customThe solvent phase was separated
  17. customThe gum was again triturated with hexane
  18. customthe solvent phase was separated
  19. customthe solvent was evaporated under reduced pressure
  20. washthe residue was washed with ether
  21. customdried to 4, as a solid, mp: 138°-140° C.

Sources & evidence

ORD record
ord-69f3c8729c2241deb4b007a068c17107
Source dataset
uspto-grants-1980_05
Patent number
US04205079

Reaction notes

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