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Potassium Iodide → HCID 19786588、化合物

HRID 1657110
ノート
印刷プレビュー

反応式

HRID 1657110 の反応式
Cl[CH2:2][CH2:3][CH2:4][CH:5]1[C:20](=[O:21])[C:9]2[C:10]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[F:19])=[N:11][O:12][C:8]=2[CH2:7][CH2:6]1.C(=O)([O-])[O-].[K+].[K+].C(N(C(C)C)CC)(C)C.[N:37]1[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=1[N:43]1[CH2:48][CH2:47][NH:46][CH2:45][CH2:44]1.[I-].[K+]>CN(C=O)C>[F:19][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=1[C:10]1[C:9]2[C:20](=[O:21])[CH:5]([CH2:4][CH2:3][CH2:2][N:46]3[CH2:47][CH2:48][N:43]([C:38]4[CH:39]=[CH:40][CH:41]=[CH:42][N:37]=4)[CH2:44][CH2:45]3)[CH2:6][CH2:7][C:8]=2[O:12][N:11]=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

7

反応物 5

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 81531DiisopropylethylamineHCID 944591-(2-Pyridyl)piperazineHCID 19786560HCID 19786560、化合物

生成物 1

HCID 19786588HCID 19786588、化合物

試薬・触媒・溶媒 1

HCID 6228
Dimethylformamide
溶媒

反応条件

温度
80 °C

実験手順

To a solution consisting of 5-(3-chloropropyl)-3-(2-fluorophenyl)-6,7-dihydro -1,2-benzisoxazol-4(5H)-one (6.4 g) and DMF (100 ml) was added anhydrous potassium carbonate (1.4 g), diisopropylethyl amine (5.4 ml), 1-(2-pyridyl)piperazine (4.8 ml) and potassium iodide (0.4 g) at room temperature with stirring. The flask was flushed with nitrogen and warmed to 80° C. for 16 hours. Upon cooling to room temperature, water and ethyl acetate were added to the reaction mixture. The layers were separated and the aqueous phase was extracted three times with ethyl acetate. The combined organic layers were washed with water twice, then brine and dried (MgSO4). Filtration and concentration gave the crude product. Purification via preparative HIPLC (silica gel, 3% methanol) afforded 4.2 g of 6,7-dihydro-3-(2-fluorophenyl)-5-[3-(4-(2-pyridyl)-1-piperazinyl)-propyl]-1,2-benzisoxazol-4(5H)-one, as an oil which solidified upon standing. The product was recrystallized from ether, m.p. 94°- 96° C.

後処理

  1. customThe flask was flushed with nitrogen
  2. temperatureUpon cooling to room temperature
  3. additionwater and ethyl acetate were added to the reaction mixture
  4. customThe layers were separated
  5. extractionthe aqueous phase was extracted three times with ethyl acetate
  6. washThe combined organic layers were washed with water twice
  7. dry with materialbrine and dried (MgSO4)
  8. filtrationFiltration and concentration
  9. customgave the crude product
  10. customPurification via preparative HIPLC (silica gel, 3% methanol)

出典と根拠

ORDレコード
ord-6db7134688e24fb79674ab2a9aa62c7d
出典データセット
uspto-grants-1993_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05256672

反応ノート

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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート