4'-Hydroxypropiophenone → Ifenprodil

HRID 355078

반응식

HRID 355078 반응식
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:11])[CH2:9][CH3:10])=[CH:4][CH:3]=1.BrBr.C([O-])(=O)C.[Na+].[CH2:19]([C:26]1[CH:31]=[CH:30][N:29]=[CH:28][CH:27]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.[H][H]>[C].[Pd].CO.O1CCOCC1>[CH3:10][CH:9]([N:29]1[CH2:30][CH2:31][CH:26]([CH2:19][C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH2:27][CH2:28]1)[CH:8]([OH:11])[C:5]1[CH:6]=[CH:7][C:2]([OH:1])=[CH:3][CH:4]=1

참가 물질

9

반응물 5

HCID 62714'-HydroxypropiophenoneHCID 164584-BenzylpyridineHCID 24408BromineHCID 517045Sodium AcetateHCID 178418361HCID 178418361, 화합물

생성물 1

HCID 3689Ifenprodil수율 72.3%

시약·촉매·용매 3

HCID 178418390HCID 178418390, 화합물촉매HCID 887Methanol용매2회HCID 312751,4-Dioxane용매

실험 절차

To 5 ml of dioxane were added 3.0 g of 4'-hydroxypropiophenone. 3.6 Grams of bromine were added dropwise to the mixture with stirring at room temperature, and the reaction liquid was stirred for an additional 10 minutes. To the reaction liquid were then added 1.7 g of anhydrous sodium acetate, 3.7 g of 4-benzylpyridine and 40 ml of methanol, and the mixture was refluxed under heating for 5 hours. After replacing the air in the reaction container with nitrogen gas, 60 ml of methanol and 3.0 g of 10% palladium-carbon were added and hydrogen was then introduced and the mixture was stirred for 8 hours at 90°-95° C. under pressure of 20 kg/cm2. The reaction mixture was then treated in the same manner as described in Example 18, whereby 4.7 g (61.0%) of ifenprodil were obtained as white crystals.

후처리

  1. customthe reaction liquid
  2. stirringwas stirred for an additional 10 minutes
  3. customTo the reaction liquid
  4. temperaturethe mixture was refluxed
  5. temperatureunder heating for 5 hours
  6. additionwere added
  7. stirringthe mixture was stirred for 8 hours at 90°-95° C. under pressure of 20 kg/cm2
  8. additionThe reaction mixture was then treated in the same manner

출처 및 근거

ORD 기록
ord-25685ddf1c9444339d43b322d2ee3acc
출처 데이터셋
uspto-grants-1983_03
특허 번호
US04377691

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