Piperazine → 5-Chloro-2-(piperazin-1-yl)benzonitrile

HRID 849488

反応式

HRID 849488 の反応式
Cl[C:2]1[CH:9]=[CH:8][C:7]([Cl:10])=[CH:6][C:3]=1[C:4]#[N:5].[NH:11]1[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]1>CN(C=O)C>[Cl:10][C:7]1[CH:8]=[CH:9][C:2]([N:11]2[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]2)=[C:3]([CH:6]=1)[C:4]#[N:5]

参加物

4

反応物 2

HCID 4837PiperazineHCID 890002,5-Dichlorobenzonitrile

生成物 1

HCID 193671275-Chloro-2-(piperazin-1-yl)benzonitrile収率 20.5%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
100 °C

実験手順

A mixture of 2,5-dichlorobenzonitrile (Lancaster; 2.994 g), piperazine (Aldrich; 7.616 g), and DMF (10 mL) is stirred for 4.5 h at 100° C. After cooling, the DMF is removed under reduced pressure and the residue is partitioned between dichloromethane and saturated aq. sodium bicarbonate. The organic layers are dried with MgSO4 and concentrated under reduced pressure. The residue is chromatographed on silica gel using methanol/dichloromethane (8/92) and the appropriate fractions are combined and concentrated to give 0.79 g of 5-chloro-2-(piperazin-1-yl)benzonitrile; MS m/z 221; IR (mineral oil) 1489, 802, 829, 2223, 845 cm-1, 1H NMR (CDCl3) δ 3.09, 3.18, 6.94, 7.43, 7.52.

後処理

  1. temperatureAfter cooling
  2. customthe DMF is removed under reduced pressure
  3. customthe residue is partitioned between dichloromethane and saturated aq. sodium bicarbonate
  4. dry with materialThe organic layers are dried with MgSO4
  5. concentrationconcentrated under reduced pressure
  6. customThe residue is chromatographed on silica gel
  7. concentrationconcentrated

出典と根拠

ORDレコード
ord-22c467f1d577466d9788be631f81d645
出典データセット
uspto-grants-2000_01
特許番号
US06013654

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