Stannous chloride dihydrate → 6-(4-Allylpiperazin-1-yl)pyridin-3-ylamine
Reaction equation
[CH2:1]([N:4]1[CH2:9][CH2:8][N:7]([C:10]2[CH:15]=[CH:14][C:13]([N+:16]([O-])=O)=[CH:12][N:11]=2)[CH2:6][CH2:5]1)[CH:2]=[CH2:3].O.O.[Sn](Cl)Cl>CO>[CH2:1]([N:4]1[CH2:5][CH2:6][N:7]([C:10]2[N:11]=[CH:12][C:13]([NH2:16])=[CH:14][CH:15]=2)[CH2:8][CH2:9]1)[CH:2]=[CH2:3]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 70 °C
Procedure
2.2 g (8.86 mmol) of 1-allyl-4-(5-nitropyridin-2-yl)piperazine from Example 1.1 were dissolved in 150 ml of methanol after which 18 g (79.75 mmol) of tin(II) chloride dihydrate were added and the mixture was stirred at 70° C. for 4 hours. After the solvent had been evaporated down to dryness, water was added to the residue. The aqueous reaction mixture was made alkaline with dilute sodium hydroxide solution and then extracted with ethyl acetate. The solid which had precipitated out was filtered off. After that, the phases were separated and the aqueous phase was extracted in each case twice with ethyl acetate and dichloromethane. The combined organic phases were dried over sodium sulfate. 1.74 g (90% of theory) of the title compound were obtained after the drying agent had been removed and the solvent had been evaporated down to dryness.
Workup
- additionwere added
- customAfter the solvent had been evaporated down to dryness, water
- additionwas added to the residue
- extractionextracted with ethyl acetate
- customThe solid which had precipitated out
- filtrationwas filtered off
- customAfter that, the phases were separated
- extractionthe aqueous phase was extracted in each case twice with ethyl acetate and dichloromethane
- dry with materialThe combined organic phases were dried over sodium sulfate
Sources & evidence
- ORD record
- ord-35496fa62dc8472ab85881482fa34b6b
- Source dataset
- uspto-grants-2013_07
- Patent number
- US08476275B2
Reaction notes
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