Ethyl Acetate → 5-Chloro-2-(methyloxy)-4-{4-[2-(methylsulfonyl)ethyl]-1-piperazinyl}aniline

HRID 419611노트

반응식

HRID 419611 반응식
[Cl:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[C:5]([O:11][CH3:12])=[CH:4][C:3]=1[N:13]1[CH2:18][CH2:17][N:16]([CH2:19][CH2:20][S:21]([CH3:24])(=[O:23])=[O:22])[CH2:15][CH2:14]1.CCOC(C)=O>CCO.[Pt]>[Cl:1][C:2]1[C:3]([N:13]2[CH2:18][CH2:17][N:16]([CH2:19][CH2:20][S:21]([CH3:24])(=[O:23])=[O:22])[CH2:15][CH2:14]2)=[CH:4][C:5]([O:11][CH3:12])=[C:6]([CH:7]=1)[NH2:8]

참가 물질

5

반응물 2

HCID 8857Ethyl AcetateHCID 594526341-[2-Chloro-5-(methyloxy)-4-nitrophenyl]-4-[2-(methylsulfonyl)ethyl]piperazine

생성물 1

HCID 594528825-Chloro-2-(methyloxy)-4-{4-[2-(methylsulfonyl)ethyl]-1-piperazinyl}aniline수율 69.3%

시약·촉매·용매 2

HCID 23939Platinum촉매HCID 702Ethanol용매

실험 절차

To 1-[2-chloro-5-(methyloxy)-4-nitrophenyl]-4-[2-(methylsulfonyl)ethyl]piperazine (1.38 g, 3.65 mmol) in EtOH (30 mL) was added EtOAc to help with solubility. The catalyst, 5% sulfided platinum on carbon (0.138 g, 0.035 mmol) was added. The reaction was placed on a Fischer-Porter Hydrogenator under 50 psi of H2 gas and was allowed to stir at rt overnight. The catalyst was filtered off and the filtrate was concentrated in vacuo, adsorbed onto silica gel and flash chromatographed. The desired fractions were combined and concentrated to give the title compound of step B (0.880 g, 69%). 1H NMR (400 MHz, DMSO-d6) δ ppm 6.58-6.70 (m, 2H), 4.64 (s, 2H), 3.74 (s, 3H), 3.22-3.37 (m, 2H), 3.04 (s, 3H), 2.84 (t, J=4.4 Hz, 4H), 2.74 (t, J=6.7 Hz, 2H), 2.50-2.63 (m, 4H).

후처리

  1. filtrationThe catalyst was filtered off
  2. concentrationthe filtrate was concentrated in vacuo
  3. customchromatographed
  4. concentrationconcentrated

출처 및 근거

ORD 기록
ord-855ce66be2864d40b726e74904379bd6
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08093239B2

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