Hydrogen Bromide → HCID 20360242, compound

HRID 436254Notes

Reaction equation

HRID 436254 reaction equation
Br.[CH3:2][C:3]12[CH2:17][CH:8]([CH:9](O)[C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=31)[CH2:7][N:6]([CH3:18])[CH2:5][CH2:4]2>O>[CH3:2][C:3]12[CH2:17][CH:8]([CH2:9][C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=31)[CH2:7][N:6]([CH3:18])[CH2:5][CH2:4]2

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 12317542HCID 12317542, compound

Product 1

HCID 20360242HCID 20360242, compoundYield 50.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

70 g of 57% hydrobromic acid, 5.5 g of red phosphorus and 18 ml of water were added to 17 g of 1,4-dimethyl-2,3,4,5,6,7-hexahydro-1,6-methano-1H-4-benzazonin-7-ol, and the mixture was heated and refluxed for 3 hours. The reaction mixture liquid was cooled and filtered, and the filtrate was subjected to distillation under reduced pressure. The residue was made alkaline with sodium hydroxide and extracted with ether. The ether extract was dried and filtered, and ether was distilled from the extract. The residue was subjected to vacuum distillation to obtain 8 g of 1,4-dimethyl-2,3,4,5,6,7-hexahydro-1,6-methano-1H-4-benzazonine boiling at 160° to 170° C. (bath temperature) under 3 mmHg in the form of a colorless oily product. When the hydrochloride was recrystallized from isopropyl alcohol, the melting point of the recrystallized product was 225° to 230° C.

Workup

  1. temperaturethe mixture was heated
  2. temperaturerefluxed for 3 hours
  3. temperatureThe reaction mixture liquid was cooled
  4. filtrationfiltered
  5. distillationthe filtrate was subjected to distillation under reduced pressure
  6. extractionextracted with ether
  7. extractionThe ether extract
  8. customwas dried
  9. filtrationfiltered
  10. distillationether was distilled from the extract
  11. distillationThe residue was subjected to vacuum distillation

Sources & evidence

ORD record
ord-54132539f86843dab91f4ee5d394f0ca
Source dataset
uspto-grants-1977_02
Patent number
US04008219

Reaction notes

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