Iodoacetamide → 2-[4-(2-Fluoro-4-nitro-phenyl)-piperazin-1-yl]-acetamide

HRID 1262387노트

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HRID 1262387 반응식
[F:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[N:11]1[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]1.I[CH2:18][C:19]([NH2:21])=[O:20].C(=O)([O-])[O-].[Cs+].[Cs+].C(#N)C>O>[F:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[N:11]1[CH2:16][CH2:15][N:14]([CH2:18][C:19]([NH2:21])=[O:20])[CH2:13][CH2:12]1

참가 물질

6

반응물 4

HCID 3727IodoacetamideHCID 6342AcetonitrileHCID 10796Cesium carbonateHCID 27830661-(2-fluoro-4-nitrophenyl)piperazine

생성물 1

HCID 471845052-[4-(2-Fluoro-4-nitro-phenyl)-piperazin-1-yl]-acetamide수율 101.9%

시약·촉매·용매 1

HCID 962Water용매

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온도
60 °C

실험 절차

1-(2-Fluoro-4-nitro-phenyl)-piperazine (0.438 g, 1.94 mmol), Iodoacetamide (0.401 g, 2.17 mmol), Cesium Carbonate (0.956 g, 2.93 mmol) and Acetonitrile (20 mL, 400 mmol) were combined and stirred at 60° C. for 20 hours. The mixture was cooled to room temperature. Water was added to the mixture and the product was extracted into ethyl acetate three times. The extracts were dried over sodium sulfate, filtered and concentrated to yield a yellow solid, 2-[4-(2-Fluoro-4-nitro-phenyl)-piperazin-1-yl]-acetamide (558 mg, 100%). LCMS: m/z=283.06 (M+H+); 1H NMR (400 MHz, DMSO-d6) δ 8.00 (d, 2H), 7.26 (br s, 1H), 7.17 (m, 2H), 2.94 (s, 2H), 2.60 (m, 2H), 2.50 (s, 6H).

후처리

  1. temperatureThe mixture was cooled to room temperature
  2. extractionthe product was extracted into ethyl acetate three times
  3. dry with materialThe extracts were dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

출처 및 근거

ORD 기록
ord-ebcd69378d2643caa0fda3fdbb80ac59
출처 데이터셋
uspto-grants-2013_06
특허 번호
US08471005B2

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