Potassium Iodide → RS-17053

HRID 1648393

反応式

HRID 1648393 の反応式
CS(O[CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[O:15][CH2:16][CH:17]1[CH2:19][CH2:18]1)(=O)=O.[I-].[K+].[Cl:22][C:23]1[CH:24]=[C:25]2[C:29](=[CH:30][CH:31]=1)[NH:28][CH:27]=[C:26]2[CH2:32][C:33]([NH2:36])([CH3:35])[CH3:34].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.O>[ClH:22].[Cl:22][C:23]1[CH:24]=[C:25]2[C:29](=[CH:30][CH:31]=1)[NH:28][CH:27]=[C:26]2[CH2:32][C:33]([NH:36][CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[O:15][CH2:16][CH:17]1[CH2:18][CH2:19]1)([CH3:34])[CH3:35]

参加物

7

反応物 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 132605-Chloro-alpha,alpha-dimethyl-1H-indole-3-ethanamineHCID 152896252-[2-(Cyclopropylmethyloxy)phenoxy]ethyl methanesulfonate

生成物 1

HCID 9824953RS-17053収率 160.4%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒2 回

反応条件

温度
120 °C

実験手順

2-[2-(cyclopropylmethyloxy)phenoxy]ethyl methanesulfonate (8.0 g, 28.0 mmol) and potassium iodide (4.65 g, 28.0 mmol) were combined in DMF and the mixture was stirred at 120° C. for 15 minutes. [2-(5-Chloro-1H-indol-3-yl)-1,1-dimethyl-ethyl]amine (4.77 g, 21.7 mmol) and potassium carbonate (5.8 g, 42.0 mmol) were added to the mixture, which was then diluted with DMF (≈50 mL) and stirred at 130°-135° C. and under nitrogen for 2 hours. The mixture was cooled, poured into water (≈800 mL), and then extracted into ether. The organic phase was separated, washed once with water and then brine, dried over magnesium sulfate, and evaporated. The residue was dissolved in ethyl acetate, 5% hydrochloric acid in methanol was added, and the solution was evaporated. The residue was dissolved in ethyl acetate and a small amount of methanol and the solution was evaporated. The residue was again dissolved in ethyl acetate and methanol and the solution was evaporated. Filtration gave [2-(5-chloro-1H-indol-3-yl)-1,1-dimethylethyl][2-(2-cyclopropylmethyloxyphenoxy)ethyl]amine hydrochloride (7.8 g, 17.4 mmol), m.p. 199°-201° C.

後処理

  1. stirringstirred at 130°-135° C. and under nitrogen for 2 hours
  2. temperatureThe mixture was cooled
  3. extractionextracted into ether
  4. customThe organic phase was separated
  5. washwashed once with water
  6. dry with materialbrine, dried over magnesium sulfate
  7. customevaporated
  8. dissolutionThe residue was dissolved in ethyl acetate
  9. addition5% hydrochloric acid in methanol was added
  10. customthe solution was evaporated
  11. dissolutionThe residue was dissolved in ethyl acetate
  12. customa small amount of methanol and the solution was evaporated
  13. dissolutionThe residue was again dissolved in ethyl acetate
  14. custommethanol and the solution was evaporated
  15. filtrationFiltration

出典と根拠

ORDレコード
ord-bf2b23efd9df45339a726ab1d0841803
出典データセット
uspto-grants-1995_07
特許番号
US05436264

関連ノート

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