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

HRID 849488

Reaction equation

HRID 849488 reaction equation
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]

Participants

4

Reactant 2

HCID 4837PiperazineHCID 890002,5-Dichlorobenzonitrile

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-22c467f1d577466d9788be631f81d645
Source dataset
uspto-grants-2000_01
Patent number
US06013654

Linked notes

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