Piperidine → HCID 58455156, 화합물

HRID 80317

반응식

HRID 80317 반응식
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:17]2[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=2)([C:10]2[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][CH:11]=2)O)=[CH:4][CH:3]=1.S(Cl)(Cl)=O.[NH:28]1[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]1>C(Cl)(Cl)Cl.C(#N)C>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:17]2[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=2)([C:10]2[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][CH:11]=2)[N:28]2[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]2)=[CH:4][CH:3]=1

참가 물질

6

반응물 3

HCID 8082PiperidineHCID 24386Thionyl ChlorideHCID 767334,4',4''-Trimethyltrityl alcohol

생성물 1

HCID 58455156HCID 58455156, 화합물수율 92%

시약·촉매·용매 2

HCID 6212Chloroform용매HCID 6342Acetonitrile용매

실험 절차

Compound 22 described above (0.17 g, 0.562 mmol) was dissolved in chloroform (4 mL) (Wako Pure Chemical Industries, Ltd.), and thionyl chloride (0.5 mL) (Wako Pure Chemical Industries, Ltd.) was added dropwise while cooling with ice. The mixture was returned to room temperature and stirred for 2 hours, and then the solvent was distilled off under reduced pressure, to thereby obtain a residue. The residue was dissolved in acetonitrile (4 mL) (Wako Pure Chemical Industries, Ltd.), and piperidine (0.19 g, 2.23 mmol) (Wako Pure Chemical Industries, Ltd.) was added thereto. The mixture was refluxed for 1 hour and allowed to cool to room temperature. The solvent was distilled off under reduced pressure, and then 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 (n-hexane (Wako Pure Chemical Industries, Ltd.) as an eluent), to thereby obtain the title compound (0.19 g, 92% yield).

후처리

  1. temperaturewhile cooling with ice
  2. customwas returned to room temperature
  3. distillationthe solvent was distilled off under reduced pressure
  4. customto thereby obtain a residue
  5. temperatureThe mixture was refluxed for 1 hour
  6. distillationThe solvent was distilled off under reduced pressure
  7. additiona saturated aqueous solution of sodium hydrogen carbonate (Wako Pure Chemical Industries, Ltd.) was added to the concentrated residue, and mixture
  8. extractionwas extracted with ethyl acetate (Wako Pure Chemical Industries, Ltd.)
  9. washThe organic layer was washed with water and brine
  10. dry with materialAfter that, the organic layer was dried with anhydrous sodium sulfate (Wako Pure Chemical Industries, Ltd.)
  11. distillationthe solvent was distilled off under reduced pressure

출처 및 근거

ORD 기록
ord-d8a233c50fc74a218dfdf21882fd3d5f
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846012B2

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