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

HRID 1262387ノート

反応式

HRID 1262387 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
60 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-ebcd69378d2643caa0fda3fdbb80ac59
出典データセット
uspto-grants-2013_06
特許番号
US08471005B2

反応ノート

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