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Sodium Iodide → (3-(4-Cyano-4-(2,4-difluorophenyl)piperidin-1-yl)propyl)carbamic acid tert-butyl ester

HRID 1066996
ノート
印刷プレビュー

反応式

HRID 1066996 の反応式
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1([C:15]#[N:16])[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]1.[C:17]([O:21][C:22]([NH:24][CH2:25][CH2:26][CH2:27]Br)=[O:23])([CH3:20])([CH3:19])[CH3:18].[I-].[Na+]>CC(C)=O>[C:17]([O:21][C:22](=[O:23])[NH:24][CH2:25][CH2:26][CH2:27][N:12]1[CH2:13][CH2:14][C:9]([C:15]#[N:16])([C:3]2[CH:4]=[CH:5][C:6]([F:8])=[CH:7][C:2]=2[F:1])[CH2:10][CH2:11]1)([CH3:20])([CH3:19])[CH3:18]
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 5238Sodium IodideHCID 4460490tert-butyl N-(3-bromopropyl)carbamateHCID 105132084-(2,4-Difluorophenyl)-piperidine-4-carbonitrile

生成物 1

HCID 18353383(3-(4-Cyano-4-(2,4-difluorophenyl)piperidin-1-yl)propyl)carbamic acid tert-butyl ester収率 75%

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

To a stirred solution of 4-(2,4-difluorophenyl)-piperidine-4-carbonitrile (0.203 g, 0.914 mmol) in acetone (20 ml), N-(tert-butoxycarbonyl)-3-bromopropylamine (0.239 g, 1.00 mmol) potassium carbonate (0.505 g, 3.65 mmol) and sodium iodide (0.274 g, 1.82 mmol) were added and the solution refluxed for 24 hours. The reaction mixture was cooled to room temperature, concentrated and partitioned between chloroform (20 mL) and water (5 mL). The organic layer was dried over sodium sulfate, filtered and concentrated. The crude product was purified by column chromatography (ethyl acetate) to yield 0.259 g (75%) of the required product as a colorless oil.

後処理

  1. temperaturethe solution refluxed for 24 hours
  2. concentrationconcentrated
  3. custompartitioned between chloroform (20 mL) and water (5 mL)
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product was purified by column chromatography (ethyl acetate)

出典と根拠

ORDレコード
ord-3cdfd36220b54f46bd16fa66b72d0afd
出典データセット
uspto-grants-2001_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06245773B1

反応ノート

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