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

HRID 849488

반응식

HRID 849488 반응식
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]

참가 물질

4

반응물 2

HCID 4837PiperazineHCID 890002,5-Dichlorobenzonitrile

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
100 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-22c467f1d577466d9788be631f81d645
출처 데이터셋
uspto-grants-2000_01
특허 번호
US06013654

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