Piperidine → 5-Bromo-3-nitro-2-(piperidin-1-yl)pyridine

HRID 1431340노트

반응식

HRID 1431340 반응식
[Br:1][C:2]1[CH:3]=[C:4]([N+:9]([O-:11])=[O:10])[C:5](Cl)=[N:6][CH:7]=1.[NH:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1>CS(C)=O.O>[Br:1][C:2]1[CH:3]=[C:4]([N+:9]([O-:11])=[O:10])[C:5]([N:12]2[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)=[N:6][CH:7]=1

참가 물질

5

반응물 2

HCID 8082PiperidineHCID 70194125-Bromo-2-chloro-3-nitropyridine

생성물 1

HCID 467387925-Bromo-3-nitro-2-(piperidin-1-yl)pyridine

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매HCID 962Water용매

반응 조건

온도
60 °C

실험 절차

To a 100 mL round bottom flask containing 5-bromo-2-chloro-3-nitropyridine (5.05 g, 21.3 mmol) in DMSO (20 mL) was added piperidine (4.2 mL, 42.6 mmol) dropwise. The reaction was heated to 60° C. and monitored with TLC and LC-MS. After 2.5 h, LC-MS showed that the reaction was complete. The mixture was cooled to rt then diluted with water. After extracting three times with EtOAc, the organic layers were combined then washed with brine and dried over anhydrous magnesium sulfate. After filtration, the mixture was concentrated under reduced pressure to afford an orange oil 5-bromo-3-nitro-2-(piperidin-1-yl)pyridine. 1H NMR (400 MHz, CDCl3) δ ppm 8.30 (1H, d, J=2.3 Hz), 8.22 (1H, d, J=2.2 Hz), 3.39 (4H, d, J=5.7 Hz), 1.75 (6H, m).

후처리

  1. temperatureThe mixture was cooled to rt
  2. extractionAfter extracting three times with EtOAc
  3. washthe organic layers were combined then washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationAfter filtration
  6. concentrationthe mixture was concentrated under reduced pressure

출처 및 근거

ORD 기록
ord-b65adad5fb4b4d34b9545c187a62426b
출처 데이터셋
uspto-grants-2015_01
특허 번호
US08940724B2

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