Hydrazine hydrate (1:1) → HCID 19744617, compound

HRID 2254411Notes

Reaction equation

HRID 2254411 reaction equation
[CH3:1][C:2]([CH3:30])([CH3:29])[C:3]#[C:4]/[CH:5]=[CH:6]/[CH2:7][N:8]([CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([C:25]([O:27][CH3:28])=O)[CH:20]=2)[CH:12]=1)[CH3:9].O.[NH2:32][NH2:33].CCCCCC.C(OCC)(=O)C>C(O)C>[CH3:1][C:2]([CH3:30])([CH3:29])[C:3]#[C:4]/[CH:5]=[CH:6]/[CH2:7][N:8]([CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([C:25]3[O:27][CH:28]=[N:32][N:33]=3)[CH:20]=2)[CH:12]=1)[CH3:9]

Participants

5

Reactant 3

HCID 24654Hydrazine hydrate (1:1)HCID 19744458HCID 19744458, compoundHCID 21226206Ethyl acetate hexane

Product 1

HCID 19744617HCID 19744617, compoundYield 10.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

173 mg of (E)-N-(6,6-dimethyl-2-hepten-4-ynyl)-N-methyl-3-(3-methoxycarbonylbenzyloxy)benzylamine was dissolved in 3 ml of ethanol, and 100 mg of 98% hydrazine hydrate was added. The mixture was heated under reflux for 3 hours. After the reaction mixture was evaporated under reduced pressure, water and ethyl acetate were added to the residue to extract it. The organic layer was separated and dried over anhydrous sodium sulfate. The desiccant was separated by filtration and the solvent was evaporated. The residual carbohydrazide was added to 4 ml of trimethyl orthoformate and the mixture was heated under reflux for 8 hours. After evaporating the excess trimethyl orthoformate, the residue was extracted with a mixture of ethyl acetate and water. The organic layer was separated and dried over anhydrous sodium sulfate. The desiccant was separated by filtration and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography Wakogel C-200, 30 g; eluting solvent: hexane/ethyl acetate=2/1] and medium-pressure liquid chromatography column: Lobar column, size A, Lichroprep Si 60 (E. Merck Co.); eluting solvent: hexane/ethyl acetate=3/1→2/1) to give 18 mg (yield 10%) of the captioned compound as a colorless oil.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 3 hours
  3. customAfter the reaction mixture was evaporated under reduced pressure, water and ethyl acetate
  4. additionwere added to the residue
  5. extractionto extract it
  6. customThe organic layer was separated
  7. dry with materialdried over anhydrous sodium sulfate
  8. customThe desiccant was separated by filtration
  9. customthe solvent was evaporated
  10. additionThe residual carbohydrazide was added to 4 ml of trimethyl orthoformate
  11. temperaturethe mixture was heated
  12. temperatureunder reflux for 8 hours
  13. customAfter evaporating the excess trimethyl orthoformate
  14. extractionthe residue was extracted with a mixture of ethyl acetate and water
  15. customThe organic layer was separated
  16. dry with materialdried over anhydrous sodium sulfate
  17. customThe desiccant was separated by filtration
  18. customthe solvent was evaporated under reduced pressure
  19. customThe residue was purified by silica gel column chromatography Wakogel C-200, 30 g

Sources & evidence

ORD record
ord-9e2c62726878471c8e26945433749ae2
Source dataset
uspto-grants-1993_08
Patent number
US05234946

Reaction notes

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