Sodium hydride → 3-[2-(4-Fluoro-phenyl)-allyl]-1,3-dimethyl-piperidin-4-one

HRID 576518

反応式

HRID 576518 の反応式
[CH3:1][N:2]1[CH2:7][CH2:6][C:5](=[O:8])[CH:4]([CH3:9])[CH2:3]1.[H-].[Na+].Br[CH2:13][C:14]([C:16]1[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=1)=[CH2:15]>CN(C=O)C>[F:22][C:19]1[CH:20]=[CH:21][C:16]([C:14](=[CH2:15])[CH2:13][C:4]2([CH3:9])[C:5](=[O:8])[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3]2)=[CH:17][CH:18]=1

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 1073111,3-Dimethyl-4-piperidoneHCID 116942121-(3-Bromoprop-1-en-2-yl)-4-fluorobenzene

生成物 1

HCID 673559603-[2-(4-Fluoro-phenyl)-allyl]-1,3-dimethyl-piperidin-4-one収率 52.1%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a stirred solution of 1,3-dimethylpiperidin-4-one (2.8 g, 22.04 mmol) in DMF (10 mL) was added sodium hydride (970 mg, 24.25 mmol) at 0° C. After stiffing for 5 min, 1-(1-bromomethyl-vinyl)-4-fluoro-benzene (4.74 g, 22.04 mmol) was added dropwise and stirring was continued for 30 min. The reaction mass was quenched with ice water and extracted with EtOAc (2×100 mL). The combined organic layer was washed with water (4×100 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by column chromatography using silica (100:200) and 10% EtOAc-Hex as eluent to yield 3 g of 3-[2-(4-fluoro-phenyl)-allyl]-1,3-dimethyl-piperidin-4-one.

後処理

  1. waitwas continued for 30 min
  2. customThe reaction mass was quenched with ice water
  3. extractionextracted with EtOAc (2×100 mL)
  4. washThe combined organic layer was washed with water (4×100 mL)
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by column chromatography

出典と根拠

ORDレコード
ord-b54513457c934568b71cafae228ac900
出典データセット
uspto-grants-2015_05
特許番号
US09040519B2

関連ノート

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