Morpholine → [2-(Morpholin-4-yl)phenyl]methanol

HRID 1678578

반응식

HRID 1678578 반응식
F[C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].[NH:10]1[CH2:15][CH2:14][O:13][CH2:12][CH2:11]1.C(=O)([O-])[O-].[K+].[K+].[BH4-].[Na+]>CN(C=O)C.CO.O>[N:10]1([C:2]2[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=2[CH2:4][OH:5])[CH2:15][CH2:14][O:13][CH2:12][CH2:11]1

참가 물질

8

반응물 4

HCID 8083MorpholineHCID 11430Potassium CarbonateHCID 67970o-FluorobenzaldehydeHCID 4311764Sodium borohydride

생성물 1

HCID 2776562[2-(Morpholin-4-yl)phenyl]methanol수율 30%

시약·촉매·용매 3

HCID 887Methanol용매HCID 962Water용매2회HCID 6228Dimethylformamide용매

반응 조건

온도
80 °C

실험 절차

2-Fluorobenzaldehyde (1.0 g, 8.1 mmol) was dissolved in DMF (20 mL), morpholine (2.0 mL) and potassium carbonate (1.1 g, 8.1 mmol) were added thereto, and then the mixture was stirred at 80° C. for 2 days. To the reaction solution was added water, and the reaction mixture was extracted with ethyl acetate. The extract was dried, and then concentrated under reduced pressure. The residue was purified with silica gel column chromatography (hexane/ethyl acetate=98:2 to 60:40) to give an oily matter. The resulting oily matter was dissolved in methanol (20 mL), sodium borohydride (613 mg, 16.2 mmol) was added thereto, and the mixture was stirred at room temperature for 3 hours. To the reaction solution was added water, and the reaction mixture was extracted with ethyl acetate. The extract was dried, and then concentrated under reduced pressure to give the title compound (474 mg, yield 30%).

후처리

  1. extractionthe reaction mixture was extracted with ethyl acetate
  2. customThe extract was dried
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified with silica gel column chromatography (hexane/ethyl acetate=98:2 to 60:40)
  5. customto give an oily matter
  6. stirringthe mixture was stirred at room temperature for 3 hours
  7. extractionthe reaction mixture was extracted with ethyl acetate
  8. customThe extract was dried
  9. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-7a1371fc483e4f009993f81201af17eb
출처 데이터셋
uspto-grants-2011_08
특허 번호
US08008525B2

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