Pyrrolidine → 1-[Bis(4-methylphenyl)methyl]pyrrolidine

HRID 80319

반응식

HRID 80319 반응식
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:10]2[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][CH:11]=2)O)=[CH:4][CH:3]=1.[NH:17]1[CH2:21][CH2:20][CH2:19][CH2:18]1.C(=O)([O-])O.[Na+]>S(Cl)(Cl)=O.C(#N)C.CO>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:10]2[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][CH:11]=2)[N:17]2[CH2:21][CH2:20][CH2:19][CH2:18]2)=[CH:4][CH:3]=1

참가 물질

7

반응물 3

HCID 31268PyrrolidineHCID 2793564,4'-DimethylbenzhydrolHCID 516892Sodium Bicarbonate

생성물 1

HCID 251462401-[Bis(4-methylphenyl)methyl]pyrrolidine수율 85.5%

시약·촉매·용매 3

HCID 887Methanol용매HCID 6342Acetonitrile용매HCID 24386Thionyl Chloride용매

실험 절차

Compound 14 (0.30 g, 1.41 mmol) was dissolved in thionyl chloride (1 mL) (Wako Pure Chemical Industries, Ltd.), and the mixture was refluxed for 2 hours. The reaction solution was concentrated under reduced pressure, to thereby obtain a residue. The residue was dissolved in acetonitrile (5 mL) (Wako Pure Chemical Industries, Ltd.), and pyrrolidine (0.50 g, 7.03 mmol) was added thereto, and the mixture was refluxed for 2 hours and then allowed to cool to room temperature. A saturated aqueous solution of sodium hydrogen carbonate (Wako Pure Chemical Industries, Ltd.) was added to the reaction solution, and then mixture was extracted with ethyl acetate. The organic layer was dried with anhydrous sodium sulfate (Wako Pure Chemical Industries, Ltd.), and the solvent was distilled off under reduced pressure. The residue was subjected to silica gel column chromatography (chloroform (Wako Pure Chemical Industries, Ltd.):methanol (Wako Pure Chemical Industries, Ltd.)=99:1 as an eluent), to thereby obtain the title compound (0.32 g, 84% yield).

후처리

  1. temperaturethe mixture was refluxed for 2 hours
  2. concentrationThe reaction solution was concentrated under reduced pressure
  3. customto thereby obtain a residue
  4. temperaturethe mixture was refluxed for 2 hours
  5. extractionmixture was extracted with ethyl acetate
  6. dry with materialThe organic layer was dried with anhydrous sodium sulfate (Wako Pure Chemical Industries, Ltd.)
  7. distillationthe solvent was distilled off under reduced pressure

출처 및 근거

ORD 기록
ord-59ffcaf6c2434db88da8e3eb9c8f939f
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846012B2

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