Piperazine → 2-Nitro-5-(1-piperazinyl)aniline

HRID 884413ノート

反応式

HRID 884413 の反応式
Cl[C:2]1[CH:3]=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([NH2:8])[CH:7]=1.[NH:12]1[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[N+:9]([C:5]1[CH:4]=[CH:3][C:2]([N:12]2[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]2)=[CH:7][C:6]=1[NH2:8])([O-:11])=[O:10]

参加物

5

反応物 3

HCID 4837PiperazineHCID 11430Potassium CarbonateHCID 742185-Chloro-2-nitroaniline

生成物 1

HCID 6021122-Nitro-5-(1-piperazinyl)aniline収率 70.2%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
150 °C

実験手順

A mixture of 5-chloro-2-nitrophenylamine (4.3 g, 25 mmol), piperazine (12.5 g, 145 mmol), and K2CO3 (4.0 g, 29 mmol) in DMF (50 mL) was stirred at 150° C. for 18 h. The reaction mixture was cooled to room temperature, solids were removed by filtration, and the filtrate was concentrated to a red residue. The residue was dissolved in EtOAc (100 mL), washed with water (50 mL), dried with Na2SO4, and concentrated in vacuo to afford the product as a yellow solid (3.9 g, 70%). See, Pharmazie, 39:747 (1984).

後処理

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customsolids were removed by filtration
  3. concentrationthe filtrate was concentrated to a red residue
  4. dissolutionThe residue was dissolved in EtOAc (100 mL)
  5. washwashed with water (50 mL)
  6. dry with materialdried with Na2SO4
  7. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-028b22c7762c46b4ba52c4a42ff92fbf
出典データセット
uspto-grants-2012_08
特許番号
US08242115B2

反応ノート

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