Piperidine → 2,3-Diphenyl-4-(piperidin-1-ylmethyl)pyridine

HRID 80306노트

반응식

HRID 80306 반응식
S(Cl)(Cl)=O.[C:5]1([C:11]2[C:12]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[N:13][CH:14]=[CH:15][C:16]=2[CH2:17]O)[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[NH:25]1[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1.C(=O)([O-])O.[Na+]>>[C:5]1([C:11]2[C:12]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[N:13][CH:14]=[CH:15][C:16]=2[CH2:17][N:25]2[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]2)[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

참가 물질

5

반응물 4

HCID 8082PiperidineHCID 24386Thionyl ChlorideHCID 516892Sodium BicarbonateHCID 67428383[Diphenyl(4-pyridyl)]methanol

생성물 1

HCID 674274232,3-Diphenyl-4-(piperidin-1-ylmethyl)pyridine수율 71%

실험 절차

Thionyl chloride (1 mL) (Wako Pure Chemical Industries, Ltd.) was added to Compound 9 described above (0.30 g, 1.15 mmol), and the mixture was refluxed for 30 minutes. Then, the solvent was distilled off under reduced pressure. The residue was dissolved in acetonitrile (20 mL), and piperidine (0.75 g, 8.80 mmol) (Wako Pure Chemical Industries, Ltd.) was added thereto, followed by reflux for 3 hours. The mixture was returned to room temperature, and then a saturated aqueous solution of sodium hydrogen carbonate (Wako Pure Chemical Industries, Ltd.) was added thereto, followed by extraction with ethyl acetate (Wako Pure Chemical Industries, Ltd.). 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.) as an eluent), to thereby obtain the title compound (0.27 g, 71% yield).

후처리

  1. temperaturethe mixture was refluxed for 30 minutes
  2. distillationThen, the solvent was distilled off under reduced pressure
  3. dissolutionThe residue was dissolved in acetonitrile (20 mL)
  4. temperatureby reflux for 3 hours
  5. customwas returned to room temperature
  6. extractionfollowed by extraction with ethyl acetate (Wako Pure Chemical Industries, Ltd.)
  7. dry with materialThe organic layer was dried with anhydrous sodium sulfate (Wako Pure Chemical Industries, Ltd.)
  8. distillationthe solvent was distilled off under reduced pressure

출처 및 근거

ORD 기록
ord-4942ef47a8bb4a0f835063670b77b5c0
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846012B2

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