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

HRID 454874ノート

反応式

HRID 454874 の反応式
[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

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
200 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-def9da2c3209465cad664517d082e6dc
出典データセット
uspto-grants-2013_07
特許番号
US08497273B2

反応ノート

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