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

HRID 454874노트

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HRID 454874 반응식
[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

참가 물질

6

반응물 3

HCID 11430Potassium CarbonateHCID 693693,5-DibromopyridineHCID 759941-Benzylpiperazine

생성물 1

HCID 534853151-Benzyl-4-(5-bromopyridin-3-yl)piperazine수율 11.4%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

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온도
200 °C

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-def9da2c3209465cad664517d082e6dc
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08497273B2

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