Piperidine → 1-[Tris(4-methoxyphenyl)methyl]piperidine

HRID 80312ノート

反応式

HRID 80312 の反応式
[CH3:1][O:2][C:3]1[CH:26]=[CH:25][C:6]([C:7](Cl)([C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=2)[C:8]2[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=2)=[CH:5][CH:4]=1.[NH:27]1[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]1>C(#N)C.CCCCCC>[CH3:1][O:2][C:3]1[CH:26]=[CH:25][C:6]([C:7]([C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=2)([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=2)[N:27]2[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]2)=[CH:5][CH:4]=1

参加物

5

反応物 2

HCID 8082PiperidineHCID 6305054,4',4''-Trimethoxytrityl chloride

生成物 1

HCID 674276561-[Tris(4-methoxyphenyl)methyl]piperidine収率 49%

試薬・触媒・溶媒 2

HCID 6342Acetonitrile溶媒HCID 8058Hexane溶媒

実験手順

4,4′,4″-trimethoxytrityl chloride (0.51 g, 1.38 mmol) (Aldrich) was dissolved in acetonitrile (8 mL) (Wako Pure Chemical Industries, Ltd.), and piperidine (0.70 g, 8.22 mmol) (Wako Pure Chemical Industries, Ltd.) was added thereto. The mixture was refluxed for 1 hour, and then the solvent was distilled off under reduced pressure. A saturated aqueous solution of sodium hydrogen carbonate (Wako Pure Chemical Industries, Ltd.) was added to the concentrated residue, and mixture was extracted with ethyl acetate (Wako Pure Chemical Industries, Ltd.). The organic layer was washed with water and brine. After that, 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 alumina column chromatography (chloroform (Wako Pure Chemical Industries, Ltd.):n-hexane (Wako Pure Chemical Industries, Ltd.)=1:4 as an eluent), to thereby obtain the title compound (0.28 g, 49% yield).

後処理

  1. temperatureThe mixture was refluxed for 1 hour
  2. distillationthe solvent was distilled off under reduced pressure
  3. additionA saturated aqueous solution of sodium hydrogen carbonate (Wako Pure Chemical Industries, Ltd.) was added to the concentrated residue, and mixture
  4. extractionwas extracted with ethyl acetate (Wako Pure Chemical Industries, Ltd.)
  5. washThe organic layer was washed with water and brine
  6. dry with materialAfter that, the 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-85dda6bb728945c5a54a50350128dcb1
出典データセット
uspto-grants-2014_09
特許番号
US08846012B2

反応ノート

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