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

HRID 80319

反応式

HRID 80319 の反応式
[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

参加物

7

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 887Methanol溶媒HCID 6342Acetonitrile溶媒HCID 24386Thionyl Chloride溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-59ffcaf6c2434db88da8e3eb9c8f939f
出典データセット
uspto-grants-2014_09
特許番号
US08846012B2

関連ノート

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