Piperidine → 2-Nitro-3-(piperidin-1-yl)aniline

HRID 334499

反応式

HRID 334499 の反応式
Cl[C:2]1[C:3]([N+:9]([O-:11])=[O:10])=[C:4]([CH:6]=[CH:7][CH:8]=1)[NH2:5].[NH:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.C(OCC)(=O)C>[N+:9]([C:3]1[C:2]([N:12]2[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)=[CH:8][CH:7]=[CH:6][C:4]=1[NH2:5])([O-:11])=[O:10]

参加物

6

反応物 3

HCID 8082PiperidineHCID 11430Potassium CarbonateHCID 1010683-Chloro-2-nitroaniline

生成物 1

HCID 125972682-Nitro-3-(piperidin-1-yl)aniline収率 70.3%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
120 °C

実験手順

To a solution of 3-chloro-2-nitroaniline (CXXI) (2.00 g, 11.6 mmol, 1 eq) and piperidine (2.95 g, 34.7 mmol, 3 eq) in DMF (60 ml) was added K2CO3 (4.78 g, 34.4 mmol, 3 eq) in one portion and the mixture was stirred at 120° C. under nitrogen overnight. The reaction mixture was diluted with ethyl acetate (60 ml) and washed with saturated NaHCO3 solution (50 mL). The organic phases were dried over Na2SO4 and concentrated in vacuo, the resultant residue was purified by silica gel column chromatography (PE:EtOAc=5:1→1:1) to give 2-nitro-3-(piperidin-1-yl)aniline (CXXII) (1.8 g, 8.14 mmol, 70.3% yield) as a black solid. ESIMS found for C11H15N3O2 m/z 222 (M+H).

後処理

  1. washwashed with saturated NaHCO3 solution (50 mL)
  2. dry with materialThe organic phases were dried over Na2SO4
  3. concentrationconcentrated in vacuo
  4. customthe resultant residue was purified by silica gel column chromatography (PE:EtOAc=5:1→1:1)

出典と根拠

ORDレコード
ord-7f8b2d13be7047229a65ac2000eb1803
出典データセット
uspto-grants-2014_11
特許番号
US08883822B2

関連ノート

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