Potassium Carbonate → 3-{3-[N-(2-(3,4-Dimethoxyphenyl)-ethyl)-N-methylamino]-propyloxy)-5-phenyl-isoxazole

HRID 1489657Notes

Reaction equation

HRID 1489657 reaction equation
[OH:1][C:2]1[CH:6]=[C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[O:4][N:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH3:19][O:20][C:21]1[CH:22]=[C:23]([CH2:29][CH2:30][N:31]([CH2:33][CH2:34][CH2:35]Cl)[CH3:32])[CH:24]=[CH:25][C:26]=1[O:27][CH3:28]>CN(C)C=O>[CH3:19][O:20][C:21]1[CH:22]=[C:23]([CH2:29][CH2:30][N:31]([CH2:33][CH2:34][CH2:35][O:1][C:2]2[CH:6]=[C:5]([C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=3)[O:4][N:3]=2)[CH3:32])[CH:24]=[CH:25][C:26]=1[O:27][CH3:28]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 577693N-(3-Chloropropyl)-3,4-dimethoxy-N-methylphenethylamineHCID 178515569HCID 178515569, compound

Product 1

HCID 229023813-{3-[N-(2-(3,4-Dimethoxyphenyl)-ethyl)-N-methylamino]-propyloxy)-5-phenyl-isoxazoleYield 56.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

3.5 g of 3-hydroxy-5-phenyl-isoxazole were dissolved in 100 ml of dimethylformamide. The solution was reacted with 3 g of finely powdered potassium carbonate and the reaction mixture was heated for 15 minutes at 100° C. in a nitrogen atmosphere. Then 5.8 g of 3-[N-(2-(3,4-dimethoxyphenyl)-ethyl)-N-methylamino]-propyl chloride were added batchwise. The reaction mixture was stirred for 4 hours at 100° C., after which the salts that formed were filtered off, the filtrate was concentrated to dryness, and the residue dissolved in methyl-tert-butyl ether. The solution was then washed with aqueous sodium carbonate solution, dried with magnesium sulfate, and concentrated to dryness. The remaining crude oily title compound that was left as a residue was purified by flash chromatography using ethyl acetate as the eluent. 4.75 g of the title compound were obtained.

Workup

  1. customafter which the salts that formed
  2. filtrationwere filtered off
  3. concentrationthe filtrate was concentrated to dryness
  4. dissolutionthe residue dissolved in methyl-tert-butyl ether
  5. washThe solution was then washed with aqueous sodium carbonate solution
  6. dry with materialdried with magnesium sulfate
  7. concentrationconcentrated to dryness
  8. waitThe remaining crude oily title compound that was left as a residue
  9. customwas purified by flash chromatography

Sources & evidence

ORD record
ord-aa77c3d8a19140eabd0d6aced5d2d84b
Source dataset
uspto-grants-1997_10
Patent number
US05679699

Reaction notes

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