Sodium Carbonate → 1-(4-Fluorobenzyl)-5,6-dihydropyridin-2-(1H)-one

HRID 1436866노트

반응식

HRID 1436866 반응식
[F:1][C:2]1[CH:23]=[CH:22][C:5]([CH2:6][N:7]2[CH2:12][CH2:11][CH2:10][CH:9](S(C3C=CC=CC=3)=O)[C:8]2=[O:21])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]2[CH2:12][CH2:11][CH:10]=[CH:9][C:8]2=[O:21])=[CH:22][CH:23]=1

참가 물질

4

반응물 2

HCID 10340Sodium CarbonateHCID 690624651-(4-Fluorobenzyl)-3-(phenylsulfinyl)piperidin-2-one

생성물 1

HCID 690647451-(4-Fluorobenzyl)-5,6-dihydropyridin-2-(1H)-one

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

To a stirred solution of 1-(4-fluorobenzyl)-3-(phenylsulfinyl)piperidin-2-one one (25 g, 74 mmol) in toluene (200 mL) was added anhydrous sodium carbonate (20 g, 190 mmol). The mixture was heated to reflux for 1.5 hours. The reaction mixture was cooled to ambient temperature and the solids were removed by filtration. The filtrate solvent was removed under vacuum and the residue was purified using silica gel column chromatography eluting with 3:1 EtOAc:hexanes. Appropriate fractions were combined and removal of the solvents under vacuum gave the title compound as a white solid. 1H NMR (400 MHz, CDCl3) δ 7.26 (m, 2H), 7.01 (m, 2H), 6.56 (dt, J=9.9, 4.2 Hz, 1H), 6.00 (dt, J=9.7, 1.8 Hz, 1H), 4.59 (s, 2H), 3.32 (t, J=7.2 Hz, 2H), 2.33 (m, 2H).

후처리

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 1.5 hours
  3. customthe solids were removed by filtration
  4. customThe filtrate solvent was removed under vacuum
  5. customthe residue was purified
  6. washeluting with 3:1 EtOAc
  7. customremoval of the solvents under vacuum

출처 및 근거

ORD 기록
ord-d39c92291ee846b59b3c756bad62b4bc
출처 데이터셋
uspto-grants-2009_11
특허 번호
US07619086B2

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