Toluene → HCID 20360239, compound

HRID 2082669Notes

Reaction equation

HRID 2082669 reaction equation
C1(C)C=CC=CC=1.[CH:8]12[CH2:22][CH:13]([C:14](=[O:21])[C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=31)[CH2:12][NH:11][CH2:10][CH2:9]2.[C:23]1([CH2:29][C:30](Cl)=O)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>C(N(CC)CC)C>[CH2:30]([N:11]1[CH2:10][CH2:9][CH:8]2[CH2:22][CH:13]([CH:14]([OH:21])[C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=32)[CH2:12]1)[CH2:29][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

5

Reactant 3

HCID 1140TolueneHCID 7679Phenylacetyl chlorideHCID 20360238HCID 20360238, compound

Product 1

HCID 20360239HCID 20360239, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

20 ml of anhydrous toluene was added to 1 g of 2,3,4,5-tetrahydro-1,6-methano-1H-4-benzazonin-7(6H)-one and 2 g of triethylamine, and 1 g of phenylacetyl chloride was added dropwise to the mixture over a period of 30 minutes under ice cooling and agitation. After completion of the dropwise addition, the mixture was agitated for 1 hour at room temperature. The reaction mixture liquid was washed twice with 50 ml of water and the toluene layer was dried with anhydrous sodium sulfate and filtered. Toluene was removed from the filtrate by distillation under reduced pressure, and the residue was dissolved in 20 ml of anhydrous dioxane and the solution was heated and refluxed for 6 hours together with 0.3 g of lithium aluminum hydride. Then, excess lithium aluminum hydride was decomposed with drops of ethyl acetate, and 50 ml of saturated aqueous solution of Rochelle salt was added and the mixture was shaken. The resulting solution was extracted with ether, and the ether extract was subjected to distillation to remove ether therefrom. The residue was subjected to vacuum distillation to obtain 0.9 g of a fraction of 4-phenethyl-2,3,4,5,6,7-hexahydro-1,6-methano-1H-4-benzazonin-7-ol boiling at 148° to 152° C. (bath temperature) under 1 mmHg. The product was a light-yellow oil.

Workup

  1. additionwas added dropwise to the mixture over a period of 30 minutes under ice cooling
  2. additionAfter completion of the dropwise addition
  3. washThe reaction mixture liquid was washed twice with 50 ml of water
  4. dry with materialthe toluene layer was dried with anhydrous sodium sulfate
  5. filtrationfiltered
  6. customToluene was removed from the filtrate by distillation under reduced pressure
  7. dissolutionthe residue was dissolved in 20 ml of anhydrous dioxane
  8. temperaturethe solution was heated
  9. temperaturerefluxed for 6 hours together with 0.3 g of lithium aluminum hydride
  10. additionwas added
  11. stirringthe mixture was shaken
  12. extractionThe resulting solution was extracted with ether
  13. extractionthe ether extract
  14. distillationwas subjected to distillation
  15. customto remove ether
  16. distillationThe residue was subjected to vacuum distillation

Sources & evidence

ORD record
ord-ecc27329eba24579986d7556296415b7
Source dataset
uspto-grants-1978_04
Patent number
US04082744

Reaction notes

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