Piperidine → 4-Piperidin-1-ylbenzonitrile

HRID 2244280노트

반응식

HRID 2244280 반응식
F[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1.[NH:10]1[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1.C(=O)([O-])[O-].[K+].[K+]>CN1CCCC1=O.O>[N:10]1([C:2]2[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=2)[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1

참가 물질

6

반응물 3

HCID 8082PiperidineHCID 11430Potassium CarbonateHCID 145174-Fluorobenzonitrile

생성물 1

HCID 7667714-Piperidin-1-ylbenzonitrile수율 92%

시약·촉매·용매 2

HCID 962Water용매HCID 13387N-methyl-2-pyrrolidone용매

반응 조건

온도
120 °C

실험 절차

A mixture of 4-fluorobenzonitrile (1 g, 8.26 mmol), piperidine (0.90 mL, 9.08 mmol) and potassium carbonate (2.28 g, 16.51 mmol) in dry 1-methyl-2-pyrrolidinone (10 mL) was stirred at 120° C. under nitrogen for 20 hours. The cooled reaction mixture was then diluted with water (100 mL) and extracted with ethyl acetate (100 mL). The organic extract was washed with water (100 mL) and brine (100 mL), dried over anhydrous magnesium sulfate, and concentrated in vacuo to afford an orange oil. Purification by flash chromatography using a solvent gradient of 1 to 7% ethyl acetate in hexane gave an orange oil that was crystallized from hexane to afford the title compound (1.41 g, 92%) as an orange crystalline solid, m.p. 54° C.

후처리

  1. customThe cooled reaction mixture
  2. extractionextracted with ethyl acetate (100 mL)
  3. extractionThe organic extract
  4. washwas washed with water (100 mL) and brine (100 mL)
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customto afford an orange oil
  8. customPurification by flash chromatography
  9. customgave an orange oil that
  10. customwas crystallized from hexane

출처 및 근거

ORD 기록
ord-e42f5c9287e24e549b5f70e9d8945dce
출처 데이터셋
uspto-grants-2010_03
특허 번호
US07678787B2

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