Sodium Hydroxide → 1-Benzyl-4-(5-fluoro-2-methoxy-phenyl)-1,2,5,6-tetrahydropyridine

HRID 1633575노트

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HRID 1633575 반응식
[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]([C:15]2[CH:20]=[C:19]([F:21])[CH:18]=[CH:17][C:16]=2[O:22][CH3:23])(O)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>C(O)(=O)C.S(=O)(=O)(O)O.CCOC(C)=O.O>[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]([C:15]2[CH:20]=[C:19]([F:21])[CH:18]=[CH:17][C:16]=2[O:22][CH3:23])=[CH:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

7

반응물 2

HCID 14798Sodium HydroxideHCID 15512819HCID 15512819, 화합물

생성물 1

HCID 155128201-Benzyl-4-(5-fluoro-2-methoxy-phenyl)-1,2,5,6-tetrahydropyridine수율 65.2%

시약·촉매·용매 4

HCID 1118Sulfuric Acid촉매HCID 176Acetic Acid용매HCID 962Water용매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of 1-benzyl-4-(5-fluoro-2-methoxy-phenyl)-4-hydroxypiperidine (1.01 g 3.20 mmole) in acetic acid (40 mL) at room temperature was added 2 drops of concentrated sulfuric acid. The resulting solution was heated to reflux, and the mixture stirred for 2 days. The mixture was cooled to room temperature and diluted with EtOAc (100 mL) and water (100 mL). The solution was basified with 50% NaOH solution until pH=10. The layers were separated and the organics washed with brine. The combined aqueous layers were extracted three times with EtOAc (50 mL). The combined organic layers were dried over Na2SO4 and concentrated. Flash chromatography (elution with 1:1 EtOAc-hexane) to give 0.62 g (65%) of 1-benzyl-4-(5-fluoro-2-methoxy-phenyl)-1,2,5,6-tetrahydropyridine as a yellow oil.

후처리

  1. temperatureThe resulting solution was heated
  2. temperatureto reflux
  3. customThe layers were separated
  4. washthe organics washed with brine
  5. extractionThe combined aqueous layers were extracted three times with EtOAc (50 mL)
  6. dry with materialThe combined organic layers were dried over Na2SO4
  7. concentrationconcentrated
  8. washFlash chromatography (elution with 1:1 EtOAc-hexane)

출처 및 근거

ORD 기록
ord-45255cc203724c07a4616fce7af15b9a
출처 데이터셋
uspto-grants-2003_01
특허 번호
US06503928B2

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