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

HRID 419611ノート

反応式

HRID 419611 の反応式
[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]

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 23939Platinum触媒HCID 702Ethanol溶媒

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-855ce66be2864d40b726e74904379bd6
出典データセット
uspto-grants-2012_01
特許番号
US08093239B2

反応ノート

読み込み中…