Quinoline → 1-[4-(7-Trifluoromethyl-benzo[b]thiophen-3-yl)-piperidin-1-yl]-ethanone

HRID 456552노트

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HRID 456552 반응식
[C:1]([N:4]1[CH2:9][CH2:8][CH:7]([C:10]2[C:11]3[CH:21]=[CH:20][CH:19]=[C:18]([C:22]([F:25])([F:24])[F:23])[C:12]=3[S:13][C:14]=2C(O)=O)[CH2:6][CH2:5]1)(=[O:3])[CH3:2].N1C2C(=CC=CC=2)C=CC=1>C(OCC)(=O)C>[F:25][C:22]([F:23])([F:24])[C:18]1[C:12]2[S:13][CH:14]=[C:10]([CH:7]3[CH2:6][CH2:5][N:4]([C:1](=[O:3])[CH3:2])[CH2:9][CH2:8]3)[C:11]=2[CH:21]=[CH:20][CH:19]=1

참가 물질

4

반응물 2

HCID 7047QuinolineHCID 231124253-(1-Acetyl-piperidin-4-yl)-7-trifluoromethyl-benzo[b]thiophene-2-carboxylic acid

생성물 1

HCID 231125051-[4-(7-Trifluoromethyl-benzo[b]thiophen-3-yl)-piperidin-1-yl]-ethanone수율 74%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

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온도
200 °C

실험 절차

A mixture of 3-(1-acetyl-piperidin-4-yl)-7-trifluoromethyl-benzo[b]thiophene-2-carboxylic acid (4.13 g, 11.1 mmol), Cu powder (0.706 g, 11.1 mmol), and quinoline (20 mL) was heated to 200° C. under nitrogen. After 10 min, no gas evolution was observed and the reaction cooled at room temperature. The mixture was diluted with ethyl acetate (100 mL), filtered through a Celite bed and the filtrate washed with 1 N HCl (2×100 mL), 5% aqueous potassium carbonate (100 mL), water (100 mL), and brine (100 mL) successively. The organics were dried over magnesium sulfate, filtered, and concentrated to give an amber oil. The oil was chromatographed on silica, eluting with 10% methanol/ethyl acetate to afford 2.69 g (74%) of the desired product as a tan solid.

후처리

  1. temperaturethe reaction cooled at room temperature
  2. filtrationfiltered through a Celite bed
  3. washthe filtrate washed with 1 N HCl (2×100 mL), 5% aqueous potassium carbonate (100 mL), water (100 mL), and brine (100 mL) successively
  4. dry with materialThe organics were dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give an amber oil
  8. customThe oil was chromatographed on silica
  9. washeluting with 10% methanol/ethyl acetate

출처 및 근거

ORD 기록
ord-a0d4d6f6ef9d4edda8e4d141db3f36f3
출처 데이터셋
uspto-grants-2007_03
특허 번호
US07186724B2

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