Hydrochloric Acid → HCID 20360233, compound

HRID 436255Notes

Reaction equation

HRID 436255 reaction equation
[CH:1]12[CH2:14][CH:6]([CH2:7][C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=31)[CH2:5][NH:4][CH2:3][CH2:2]2.C(=O)(O)[O-].[Na+].[CH2:20](Br)[CH:21]=[CH2:22].[ClH:24]>CCOCC.CO>[ClH:24].[CH2:22]([N:4]1[CH2:3][CH2:2][CH:1]2[CH2:14][CH:6]([CH2:7][C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=32)[CH2:5]1)[CH:21]=[CH2:20]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7841Allyl bromideHCID 516892Sodium BicarbonateHCID 20026446HCID 20026446, compound

Product 1

HCID 20360233HCID 20360233, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Procedure

1.87 g of 2,3,4,5,6,7-hexahydro-1,6-methano-1H-4-benzazonine, 1.25 g of sodium bicarbonate and 1.33 g of allyl bromide were added into 30 ml of methanol, and the mixture was refluxed for 5 hours and subjected to distillation under reduced pressure. The residue was dissolved in 15 ml of 10% hydrochloric acid. The solution was washed once with 5 ml of benzene, and the water layer was made alkaline with sodium hydroxide and extracted with ether. Ether was distilled from the ether extract and the residue was subjected to vacuum distillation to obtain 2 g of a colorless oily substance as a fraction boiling at 110° to 120° C. (bath temperature) under 0.7 mmHg. The product was dissolved in 15 ml of ether and gaseous hydrochloric acid was blown into the solution to form a white precipitate. The precipitate was recovered by filtration and dried to obtain 4-allyl-2,3,4,5,6,7-hexahydro-1,6-methano-1H-4-benzazonine hydrochloride. Recrystallization from isopropanol gave a white crystalline powder melting at 212.5° to 214.5° C.

Workup

  1. temperaturethe mixture was refluxed for 5 hours
  2. distillationsubjected to distillation under reduced pressure
  3. dissolutionThe residue was dissolved in 15 ml of 10% hydrochloric acid
  4. washThe solution was washed once with 5 ml of benzene
  5. extractionextracted with ether
  6. distillationEther was distilled from the ether
  7. extractionextract
  8. distillationthe residue was subjected to vacuum distillation
  9. customto obtain 2 g of a colorless oily substance as a fraction boiling at 110° to 120° C. (bath temperature) under 0.7 mmHg
  10. customto form a white precipitate
  11. filtrationThe precipitate was recovered by filtration
  12. customdried

Sources & evidence

ORD record
ord-7c41c894befe42b4a3ed7c0eba53dc6c
Source dataset
uspto-grants-1977_02
Patent number
US04008219

Reaction notes

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