Potassium Carbonate → 3-{3-[N-(2-(3,4-Dimethoxyphenyl)-ethyl)-N-methylamino]-propyloxy}-5-(3,4-dimethoxyphenyl)-pyrazole

HRID 1489642

反応式

HRID 1489642 の反応式
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]2[NH:15][NH:14][C:13](=[O:16])[CH2:12]2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].C(=O)([O-])[O-].[K+].[K+].[CH3:23][O:24][C:25]1[CH:26]=[C:27]([CH2:33][CH2:34][N:35]([CH2:37][CH2:38][CH2:39]Cl)[CH3:36])[CH:28]=[CH:29][C:30]=1[O:31][CH3:32]>CN(C)C=O>[CH3:23][O:24][C:25]1[CH:26]=[C:27]([CH2:33][CH2:34][N:35]([CH2:37][CH2:38][CH2:39][O:16][C:13]2[CH:12]=[C:11]([C:5]3[CH:6]=[CH:7][C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=3)[NH:15][N:14]=2)[CH3:36])[CH:28]=[CH:29][C:30]=1[O:31][CH3:32]

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 577693N-(3-Chloropropyl)-3,4-dimethoxy-N-methylphenethylamineHCID 220460885-(3,4-Dimethoxyphenyl)-pyrazolin-3-one

生成物 1

HCID 152835203-{3-[N-(2-(3,4-Dimethoxyphenyl)-ethyl)-N-methylamino]-propyloxy}-5-(3,4-dimethoxyphenyl)-pyrazole収率 64%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

反応条件

温度
100 °C

実験手順

17 g of 5-(3,4-dimethoxyphenyl)-pyrazolin-3-one were dissolved in 200 ml of dimethylformamide. 11 g of potassium carbonate were added to the solution and the reaction mixture was heated at 100° C. under a nitrogen atmosphere for 0.5 hours. A solution of 21 g of 3-[N-(2-(3,4-di-methoxyphenyl)-ethyl)-N-methylamino]-propylchloride in 150 ml of dimethylformamide was then added dropwise. After 2 hours the salts which formed were filtered out, the filtrate was evaporated to dryness, and the residue was dissolved in ethyl acetate. The solution was subsequently washed with 7% strength aqueous sodium hydroxide solution in order to remove unreacted 5-(3,4-dimethoxyphenyl)-pyrazolin-3-one, dried with sodium sulfate and evaporated to dryness. The residue which remained was 35 g of oily crude product. This product was purified by chromatography over finely particulate silica gel under slightly elevated pressure (flash chromatography) using tert-butyl methyl ether/methanol 10:1 as eluent. 22.3 g of the title compound were obtained as an oil. IR spectrum of the base (as film): 1513 cm-1, 1260 cm-1, 1236 cm-1.

後処理

  1. customAfter 2 hours the salts which formed
  2. filtrationwere filtered out
  3. customthe filtrate was evaporated to dryness
  4. dissolutionthe residue was dissolved in ethyl acetate
  5. washThe solution was subsequently washed with 7% strength aqueous sodium hydroxide solution in order
  6. customto remove unreacted 5-(3,4-dimethoxyphenyl)-pyrazolin-3-one
  7. dry with materialdried with sodium sulfate
  8. customevaporated to dryness
  9. customThis product was purified by chromatography over finely particulate silica gel under slightly elevated pressure (flash chromatography)

出典と根拠

ORDレコード
ord-3658cdd99d2e4a0dbba550bcfc88b37b
出典データセット
uspto-grants-1997_10
特許番号
US05679699

関連ノート

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