Potassium Carbonate → 1-Benzyl-4-(5-bromopyridin-3-yl)piperazine

HRID 454874Notes

Reaction equation

[CH2:1]([N:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:14][C:15]1[CH:16]=[N:17][CH:18]=[C:19](Br)[CH:20]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.O>[CH2:1]([N:8]1[CH2:13][CH2:12][N:11]([C:19]2[CH:18]=[N:17][CH:16]=[C:15]([Br:14])[CH:20]=2)[CH2:10][CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 200 °C

Procedure

A mixture of 1-benzyl-piperazine (1.49 g, 8.44 mmol), 3,5-dibromo-pyridine (2.00 g, 8.44 mmol), and potassium carbonate (1.17 g, 8.44 mmol) in 15 ml DMF was heated at 200° C. for 1 h under a nitrogen atmosphere. Then the mixture was diluted with 100 ml of water and was extracted twice with ethyl acetate. The combined organic layers were extracted with aqueous HCl solution. The pH of the aqueous solution was adjusted to pH 10 with aqueous NaOH. After extraction with diethylether the combined organic phases were dried with magnesium sulfate, filtered and the solvent was evaporated under reduced pressure. The so obtained oil was purified via silica gel chromatography with cyclohexane/ethyl acetate (2:1) as eluent to give 0.32 g of the product.

Workup

extractionwas extracted twice with ethyl acetate
extractionThe combined organic layers were extracted with aqueous HCl solution
extractionAfter extraction with diethylether the combined organic phases
dry with materialwere dried with magnesium sulfate
filtrationfiltered
customthe solvent was evaporated under reduced pressure
customThe so obtained oil was purified via silica gel chromatography with cyclohexane/ethyl acetate (2:1) as eluent

Sources & evidence

ORD record: ord-def9da2c3209465cad664517d082e6dc
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08497273B2

Reaction notes

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