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

HRID 1078357

反応式

HRID 1078357 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
100 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-51ebbcea8b71460892112ccfb9e57b40
出典データセット
uspto-grants-1996_08
特許番号
US05547967

関連ノート

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