Piperazine → 3-Fluoro-4-piperazin-1-yl-benzonitrile

HRID 875013ノート

反応式

HRID 875013 の反応式
[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1F)[C:5]#[N:6].[NH:11]1[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]1>CN(C)C(=O)C.O>[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[N:11]1[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]1)[C:5]#[N:6]

参加物

5

反応物 2

HCID 4837PiperazineHCID 5872033,4-Difluorobenzonitrile

生成物 1

HCID 5961133-Fluoro-4-piperazin-1-yl-benzonitrile収率 95.4%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 31374Dimethylacetamide溶媒

反応条件

温度
120 °C

実験手順

3,4-Difluorobenzonitrile (2.0 g, 14.3 mmol) and piperazine (6.19 g, 71.8 mmol) were dissolved in N,N-dimethylacetamide (10 mL) and the solution was heated to 120° C. for 1.5 h. The reaction mixture was cooled to room temperature, diluted with water, and extracted with EtOAc. The combined extracts were washed with water and brine, dried over anhydrous Na2SO4, and concentrated under reduced pressure to get 3-fluoro-4-(piperazin-1-yl)benzonitrile (2.8 g, yield 95%), which was carried through without further purification. 1H NMR (400 MHz, DMSO-d6) δ 7.69-7.65 (dd, J=13.6 Hz, 2.0 Hz, 1H), 7.56-7.53 (dd, J=8.5 Hz, 1.8 Hz, 1H), 7.12-7.07 (d, J=8.7 Hz, 1H), 3.08-3.05 (m, 4H), 2.83-2.80 (m, 4H). MS (ESI) m/z: Calculated for C11H12FN3: 205.10. found: 205.9 (M+H)+

後処理

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionextracted with EtOAc
  3. washThe combined extracts were washed with water and brine
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-ddb9d8bb25a641a8a773d0704335ff56
出典データセット
uspto-grants-2015_03
特許番号
US08981084B2

反応ノート

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