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

HRID 1431340ノート

反応式

HRID 1431340 の反応式
[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

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 679Dimethyl Sulfoxide溶媒HCID 962Water溶媒

反応条件

温度
60 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-b65adad5fb4b4d34b9545c187a62426b
出典データセット
uspto-grants-2015_01
特許番号
US08940724B2

反応ノート

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