Potassium Carbonate → 1-Allyl-4-(5-nitropyridin-2-yl)piperazine
Reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:17]([N:20]1[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]1)[CH:18]=[CH2:19]>CN(C)C=O>[CH2:17]([N:20]1[CH2:25][CH2:24][N:23]([C:2]2[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=2)[CH2:22][CH2:21]1)[CH:18]=[CH2:19]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
2.0 g (12.61 mmol) of 2-chloro-5-nitropyridine were dissolved in 8 ml of dimethylformamide, and 3.49 g (25.23 mmol) of potassium carbonate were added. After that, a solution of 1.75 g (13.88 mmol) of N-allylpiperazine in 2 ml of dimethylformamide was added slowly dropwise to the reaction mixture (exothermic reaction). The reaction mixture was then stirred at room temperature for 2 hours. After the solvent had been concentrated down to dryness, the resulting residue was stirred up in 100 ml of heptane. The precipitate which remained was filtered off with suction. The filtrate was concentrated, resulting in 720 mg of the title compound. The precipitate which had been filtered off with suction was treated with 150 ml of water and extracted three times with diethyl ether. The organic phase was washed with a saturated solution of sodium chloride and dried over sodium sulfate. A further 2.24 g of the title compound were isolated after the solvent had been filtered and concentrated down to dryness. The total yield of 1-allyl-4-(5-nitropyridin-2-yl)piperazine was 2.96 g (95% of theory).
Workup
- concentrationAfter the solvent had been concentrated down to dryness
- stirringthe resulting residue was stirred up in 100 ml of heptane
- filtrationThe precipitate which remained was filtered off with suction
- concentrationThe filtrate was concentrated
Sources & evidence
- ORD record
- ord-2dbce81032684078acf47967ca21d03c
- Source dataset
- uspto-grants-2008_01
- Patent number
- US07320979B2
Reaction notes
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