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Potassium Iodide → 4-(4-Chlorophenyl)-1-[3-(6-fluoro-1,2-benzisoxazol-3-yl)propyl]-1,2,3,6-tetrahydropyridine oxalate

HRID 280888
ノート
印刷プレビュー

反応式

HRID 280888 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH2:9][CH2:10][NH:11][CH2:12][CH:13]=2)=[CH:4][CH:3]=1.Cl[CH2:15][CH2:16][CH2:17][C:18]1[C:22]2[CH:23]=[CH:24][C:25]([F:27])=[CH:26][C:21]=2[O:20][N:19]=1.[C:28](=[O:31])([OH:30])[O-].[Na+].[I-].[K+].CN(C)C=[O:38]>>[C:21]([OH:20])(=[O:38])[C:28]([OH:30])=[O:31].[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH2:13][CH2:12][N:11]([CH2:15][CH2:16][CH2:17][C:18]3[C:22]4[CH:23]=[CH:24][C:25]([F:27])=[CH:26][C:21]=4[O:20][N:19]=3)[CH2:10][CH:9]=2)=[CH:4][CH:3]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 5

HCID 4875Potassium IodideHCID 6228DimethylformamideHCID 1857174-(4-Chlorophenyl)-1,2,3,6-tetrahydropyridineHCID 516892Sodium BicarbonateHCID 109108803-(3-Chloropropyl)-6-fluorobenzo[d]isoxazole

生成物 1

HCID 133198864-(4-Chlorophenyl)-1-[3-(6-fluoro-1,2-benzisoxazol-3-yl)propyl]-1,2,3,6-tetrahydropyridine oxalate
収率 56%

反応条件

温度
80 °C

実験手順

To 35 ml of dry dimethylformamide was added, 3.7 g of 4-(4-chlorophenyl)-1,2,3,6-tetrahydropyridine, 4.2 g of 3-(3-chloropropyl)-6-fluoro-1,2-benzisoxazole, 10 g of sodium bicarbonate, and a few crystals of potassium iodide. After stirring at 80° C. for one hr, the mixture was cooled, filtered and the filtrate was evaporated to an oil. The oil was stirred with 100 ml of water for five mins and then extracted with ether/ethyl acetate. The organic extract was washed with water (2x), saturated sodium chloride solution and dried over anhydrous magnesium sulfate. After filtering, the solvents were evaporated to an oil. The oil was dissolved in ether, filtered and treated with ethereal oxalic acid solution to give 5.2 g (56%) of product, mp 185° C. (dec). Two recrystallizations from ethyl acetate/methanol (9:1) gave the analytical sample, mp 207°-209° C. (dec).

後処理

  1. temperaturethe mixture was cooled
  2. filtrationfiltered
  3. customthe filtrate was evaporated to an oil
  4. stirringThe oil was stirred with 100 ml of water for five mins
  5. extractionextracted with ether/ethyl acetate
  6. extractionThe organic extract
  7. washwas washed with water (2x), saturated sodium chloride solution
  8. dry with materialdried over anhydrous magnesium sulfate
  9. filtrationAfter filtering
  10. customthe solvents were evaporated to an oil
  11. dissolutionThe oil was dissolved in ether
  12. filtrationfiltered
  13. additiontreated with ethereal oxalic acid solution

出典と根拠

ORDレコード
ord-b3394510bbb84ca7a501b93cdeeef560
出典データセット
uspto-grants-1986_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04591586

反応ノート

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