Piperazine → 3-(Piperazin-1-yl)isoquinoline

HRID 401501Notes

Reaction equation

HRID 401501 reaction equation
Cl[C:2]1[N:3]=[CH:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.[NH:12]1[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1>C(O)CO>[N:12]1([C:2]2[N:3]=[CH:4][C:5]3[C:10]([CH:11]=2)=[CH:9][CH:8]=[CH:7][CH:6]=3)[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1

Participants

4

Reactant 2

HCID 4837PiperazineHCID 6409683-Chloroisoquinoline

Product 1

HCID 130255693-(Piperazin-1-yl)isoquinolineYield 50.3%

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 3-chloroisoquinoline (200 mg, 1.22 mmol) and piperazine (2.10 g, 24.4 mmol) in ethylene glycol (2 ml) was heated to 150° C. and stirred at that temperature for 24 hours. The reaction was allowed to cool down to room temperature. The crude mixture was partitioned between water and ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate, filtered and concentrated under vacuo. The residue was and purified on silica gel by flash column chromatography to give the title compound as a pale brown solid (131 mg, 50% yield).

Workup

  1. temperatureto cool down to room temperature
  2. customThe crude mixture was partitioned between water and ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under vacuo
  7. custompurified on silica gel by flash column chromatography

Sources & evidence

ORD record
ord-e0a3dd3b7d5f429e93a763cfcf4dc801
Source dataset
uspto-grants-2014_06
Patent number
US08741931B2

Reaction notes

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