Benzene → HCID 21404764, compound

HRID 596820Notes

Reaction equation

HRID 596820 reaction equation
[CH3:1][N:2]([CH3:19])[CH2:3][C:4]([C:6]1(O)[C:15]2[CH:14]=[N:13][C:12]([O:16][CH3:17])=[CH:11][C:10]=2[CH2:9][CH2:8][CH2:7]1)=[CH2:5].C1C=CC=CC=1.P(Cl)(Cl)(Cl)=O.[OH-].[Na+]>CCOCC.O.N1C=CC=CC=1>[CH3:19][N:2]([CH3:1])[CH2:3][C:4]([C:6]1[C:15]2[CH:14]=[N:13][C:12]([O:16][CH3:17])=[CH:11][C:10]=2[CH2:9][CH2:8][CH:7]=1)=[CH2:5]

Participants

8

Reactant 4

HCID 241BenzeneHCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 21404754HCID 21404754, compound

Product 1

HCID 21404764HCID 21404764, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1049PyridineSolventHCID 3283Diethyl EtherSolvent

Procedure

To 7.1 parts of N,N-dimethyl-N-(2-[5,6,7,8tetrahydro-8-hydroxy-3-methoxyisoquinol-8-yl]prop-2-en1-yl)amine in 31 parts of benzene and 34.5 parts of pyridine is added 4.5 parts of phosphorous oxychloride, dropwise and at room temperature. That solution is stirred at room temperature for several hours, then cooled in an ice bath. 25 Parts of water slowly is added followed by enough 5% aqueous sodium hydroxide solution to bring the pH of the solution to about 10. Ether is added and the organic and aqueous layers separated. The aqueous layer is extracted with ether and the extracts washed with saturated sodium chloride and dried over anhydrous sodium sulfate. Approximately 200 parts of n-hexane is added to the solution, followed by a portion of charcoal. That mixture is filtered through diatomaceous earth to give a light yellow solution which, upon solvent removal, affords a yellow oil yielding upon crystallization N,N-dimethyl-N-(2-[5,6dihydro-3-methoxyisoquinol-8-yl]prop-2-en-1-yl)amine. A portion of that material is distilled and the distillate is taken up into methanol-water and upon standing yields crystals melting at about 42°-45°. That compound further exhibits an ultraviolet maximum in methanol at about 262 milimicrons with a molecular extinction coefficient of 12,900. It is further characterized by peaks in the nuclear magnetic resonance spectrum in deuteriochloroform at 134, 286, 336, 318, 357, 395 and 480 Hertz.

Workup

  1. customat room temperature
  2. temperaturecooled in an ice bath
  3. customthe organic and aqueous layers separated
  4. extractionThe aqueous layer is extracted with ether
  5. washthe extracts washed with saturated sodium chloride
  6. dry with materialdried over anhydrous sodium sulfate
  7. additionApproximately 200 parts of n-hexane is added to the solution
  8. filtrationThat mixture is filtered through diatomaceous earth
  9. customto give a light yellow solution which
  10. customupon solvent removal
  11. customaffords a yellow oil

Sources & evidence

ORD record
ord-0ebbbc897ef247148feaaf14f5fcb4b6
Source dataset
uspto-grants-1977_03
Patent number
US04012391

Reaction notes

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