Piperazine → 2-(Piperazin-1-yl)-6-(trifluoromethyl)quinoline

HRID 1772212ノート

反応式

HRID 1772212 の反応式
C[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:12]([F:15])([F:14])[F:13])[CH:8]=2)[N:3]=1.[NH:16]1[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[N:16]1([C:2]2[CH:11]=[CH:10][C:9]3[C:4](=[CH:5][CH:6]=[C:7]([C:12]([F:13])([F:14])[F:15])[CH:8]=3)[N:3]=2)[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1

参加物

5

反応物 3

HCID 4837PiperazineHCID 11430Potassium CarbonateHCID 112987822-Methyl-6-(trifluoromethyl)quinoline

生成物 1

HCID 867194712-(Piperazin-1-yl)-6-(trifluoromethyl)quinoline収率 65.1%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
140 °C

実験手順

To a solution of 2-methyl-6-(trifluoromethyl)quinoline (1.5 g, 7.10 mmol) in N,N-dimethylformamide (50 ml) was added piperazine (2.8 g, 32.51 mmol) and potassium carbonate (1.8 g, 12.93 mmol). The resulting solution was stirred for 3 hours at 140° C. and then quenched by the addition of water (200 ml). The crude product was extracted with ethyl acetate (3×100 ml) and the organic layers were combined. The resulting mixture was washed with saturated aqueous sodium chloride (3×100 ml), dried over anhydrous sodium sulfate, filtered, and then concentrated under vacuum. The crude residue was purified by silica gel chromatography using 1-5% methanol in dichloromethane to elute. The product-containing fractions were combined and concentrated to afford 2-(piperazin-1-yl)-6-(trifluoromethyl)quinoline as a brown solid (1.3 g, 65%). (ES, m/z): [M+H]+ 282; 1H NMR (300 MHz, DMSO): δ 8.17-8.23 (t, J=9.3, 2H), 7.66-7.77 (m, 2H), 7.63 (d, J=9.3 Hz, 1H), 3.78-3.81 (t, J=4.5 Hz, 4H), 2.92-2.96 (t, J=4.5 Hz, 4H).

後処理

  1. customquenched by the addition of water (200 ml)
  2. extractionThe crude product was extracted with ethyl acetate (3×100 ml)
  3. washThe resulting mixture was washed with saturated aqueous sodium chloride (3×100 ml)
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum
  7. customThe crude residue was purified by silica gel chromatography
  8. washto elute
  9. concentrationconcentrated

出典と根拠

ORDレコード
ord-4849afe00e9b49fea887964292d4b8b0
出典データセット
uspto-grants-2016_02
特許番号
US09249102B2

反応ノート

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