Piperazine → 1-(3-Chloropyridin-2-yl)piperazine
Reaction equation
Cl[C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][N:3]=1.[NH:9]1[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]1.C(N(CC)CC)C>CS(C)=O>[Cl:8][C:7]1[C:2]([N:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)=[N:3][CH:4]=[CH:5][CH:6]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
2,3-Dichloropyridine (15.0 g, 101.6 mmol), piperazine(9.78 g, 113.70 mmol), and triethylamine (14.36 g, 141.95 mmol) were dissolved in 300 mL of DMSO and the resulting mixture was heated at about 80° C. for about 24 h. The reaction mixture was then cooled to room temperature and extracted with a saturated aqueous sodium bicarbonate solution. The organic layer was dried, concentrated, and purified using a silica gel column eluted with a gradient elution from ethyl acetate to 2:1 ethyl acetate:methanol to provide N-(3-chloropyridin-2-yl)-piperazine (compound 1) as a yellow liquid.
Workup
- temperatureThe reaction mixture was then cooled to room temperature
- extractionextracted with a saturated aqueous sodium bicarbonate solution
- customThe organic layer was dried
- concentrationconcentrated
- custompurified
- washeluted with a gradient elution from ethyl acetate to 2:1 ethyl acetate
Sources & evidence
- ORD record
- ord-bde381ca299a47819fd5623d1756365a
- Source dataset
- uspto-grants-2007_10
- Patent number
- US07279493B2
Reaction notes
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