2-Chloropyrimidine → 1-Pyrimidin-2-yl-piperidin-4-one

HRID 1619206ノート

反応式

HRID 1619206 の反応式
Cl[C:2]1[N:7]=[CH:6][CH:5]=[CH:4][N:3]=1.O.Cl.[NH:10]1[CH2:15][CH2:14][C:13](=[O:16])[CH2:12][CH2:11]1>O1CCOCC1>[N:3]1[CH:4]=[CH:5][CH:6]=[N:7][C:2]=1[N:10]1[CH2:15][CH2:14][C:13](=[O:16])[CH2:12][CH2:11]1

参加物

4

反応物 2

HCID 744042-ChloropyrimidineHCID 2723901Piperonylamine

生成物 1

HCID 14788561-Pyrimidin-2-yl-piperidin-4-one収率 69%

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

反応条件

温度
80 °C

実験手順

To a solution of 2-chloropyrimidine (300 mg, 2.619 mmol) in dioxane (5 ml), was added piperidin-4-one hydrochloride monohydrate (402.3 mg, 2.619 mmol) at room temperature. The mixture was heated at 80° C. overnight and concentrated under reduced pressure. The residue was treated with EtOAc (30 ml) and saturated NaHCO3 (10 ml). After separation of the layers, the aqueous phase was extracted with EtOAc (2×10 ml). The combined organic layers were washed with brine (10 ml), dried (MgSO4), filtered, and concentrated under reduced pressure to furnish a crude product. This material was purified by column chromatography (40% EtOAc/hexanes) to give 1-pyrimidin-2-yl-piperidin-4-one (320 mg, 53%) as an off-white solid: 1H NMR (CDCl3, 400 MHz) δ 8.38 (d, J=6.4 Hz, 2H), 6.61 (t, J=6.4 Hz, 9H), 4.16 (t, J=5.6 Hz, 2H), 2.53 (t, J=5.6 Hz, 2H).

後処理

  1. concentrationconcentrated under reduced pressure
  2. additionThe residue was treated with EtOAc (30 ml) and saturated NaHCO3 (10 ml)
  3. customAfter separation of the layers
  4. extractionthe aqueous phase was extracted with EtOAc (2×10 ml)
  5. washThe combined organic layers were washed with brine (10 ml)
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customto furnish a crude product
  10. customThis material was purified by column chromatography (40% EtOAc/hexanes)

出典と根拠

ORDレコード
ord-b369c92272ea42f5b36121aa19dfa4b5
出典データセット
uspto-grants-2014_07
特許番号
US08772291B2

反応ノート

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