Reaction equation
[NH:1]1[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.Br[C:8]1[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=1>CC1C=CC=CC=1C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[N:10]1[CH:11]=[CH:12][CH:13]=[C:8]([N:1]2[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]2)[CH:9]=1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 120 °C
Procedure
A 500 ml Kjeldahl flask equipped with a cooling condenser and a thermometer was charged with a solution of 44.6 g of piperazine in 45 ml of o-xylene, a solution of 13.44 g of 3-bromopyridine in 45 ml of o-xylene, and a solution of 11.3 g of NaOBut in 45 ml of o-xylene, and further with a solution of 19 mg of palladium acetate in 10 ml of o-xylene (the ratio of palladium atom/heterocyclic aromatic halide=0.1% by mole). The flask was flushed with nitrogen for about 20 minutes while the content was stirred, and 0.26 ml of a solution in toluene of tri-tert.-butylphosphine having a concentration of 0.256 g/ml was added. Then the mixture was heated to 120° C., and maintained at that temperature for 3 hours with stirring. After completion of the reaction, the same treatment as employed in Example 1 was conducted to give colorless oily 1-(3-pyridyl)piperazine. The yield was 86% by mole.
Workup
- customA 500 ml Kjeldahl flask equipped with a cooling condenser
- customThe flask was flushed with nitrogen for about 20 minutes while the content
- addition0.26 ml of a solution in toluene of tri-tert.-butylphosphine having a concentration of 0.256 g/ml was added
- temperaturemaintained at that temperature for 3 hours
- stirringwith stirring
- customAfter completion of the reaction
Sources & evidence
- ORD record
- ord-846733b7bf3242d4afa79aeadbf31362
- Source dataset
- uspto-grants-1999_07
- Patent number
- US05929281
Linked notes
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