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

HRID 334499

반응식

HRID 334499 반응식
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]

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

반응 조건

온도
120 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-7f8b2d13be7047229a65ac2000eb1803
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08883822B2

연결된 노트

불러오는 중…