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Dichloromethane ethanol → 6-Chloro-2-[1-(4,4-difluorocyclohexyl)piperidin-4-yl]-3-oxo-2,3-dihydro-1H-isoindole-4-carbonitrile

HRID 333218
ノート
印刷プレビュー

反応式

HRID 333218 の反応式
[F:1][C:2]1([F:26])[CH2:7][CH2:6][CH:5]([N:8]2[CH2:13][CH2:12][CH:11]([N:14]3[CH2:22][C:21]4[C:16](=[C:17](I)[CH:18]=[C:19]([Cl:23])[CH:20]=4)[C:15]3=[O:25])[CH2:10][CH2:9]2)[CH2:4][CH2:3]1.[Cu][C:28]#[N:29].ClCCl.C(O)C>CN(C)C=O>[Cl:23][C:19]1[CH:18]=[C:17]([C:28]#[N:29])[C:16]2[C:15](=[O:25])[N:14]([CH:11]3[CH2:12][CH2:13][N:8]([CH:5]4[CH2:6][CH2:7][C:2]([F:26])([F:1])[CH2:3][CH2:4]4)[CH2:9][CH2:10]3)[CH2:22][C:21]=2[CH:20]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 21584144Dichloromethane ethanolHCID 671930032-[1-(4,4-Difluorocyclohexyl)piperidin-4-yl]-5-chloro-7-iodo-2,3-dihydro-1H-isoindol-1-oneHCID 178418546HCID 178418546、化合物

生成物 1

HCID 696740676-Chloro-2-[1-(4,4-difluorocyclohexyl)piperidin-4-yl]-3-oxo-2,3-dihydro-1H-isoindole-4-carbonitrile収率 73%

試薬・触媒・溶媒 1

HCID 6228
Dimethylformamide
溶媒

実験手順

2-[1-(4,4-Difluorocyclohexyl)piperidin-4-yl]-5-chloro-7-iodo-2,3-dihydro-1H-isoindol-1-one (80 mg, 0.16 mmol) and copper(I) cyanide (22 mg, 0.24 mmol) were dissolved in N,N-dimethylformamide (1 mL) and the resulted solution was refluxed under nitrogen atmosphere for 3 hours. The solvent was removed under reduced pressure and the residue was diluted with dichloromethane and washed with 15% ammonium hydroxide. Organic phase was dried over sodium sulfate, filtered and evaporated. Column chromatography (dichloromethane/ethanol:95/5) afforded title compound (46 mg, 72% yield).

後処理

  1. temperaturethe resulted solution was refluxed under nitrogen atmosphere for 3 hours
  2. customThe solvent was removed under reduced pressure
  3. additionthe residue was diluted with dichloromethane
  4. washwashed with 15% ammonium hydroxide
  5. dry with materialOrganic phase was dried over sodium sulfate
  6. filtrationfiltered
  7. customevaporated

出典と根拠

ORDレコード
ord-a0487bacef4c4a249ceef1c129e6d711
出典データセット
uspto-grants-2014_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08877944B2

反応ノート

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