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

HRID 1619206노트

반응식

HRID 1619206 반응식
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

참가 물질

4

반응물 2

HCID 744042-ChloropyrimidineHCID 2723901Piperonylamine

생성물 1

HCID 14788561-Pyrimidin-2-yl-piperidin-4-one수율 69%

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

반응 조건

온도
80 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-b369c92272ea42f5b36121aa19dfa4b5
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08772291B2

반응 노트

불러오는 중…