Dimethyl Sulfoxide → 1-(1-Benzylpiperidin-4-yl)-2-(2-fluorophenyl)ethanone

HRID 606154

반응식

HRID 606154 반응식
C(Cl)(=O)C(Cl)=O.CS(C)=O.[CH2:11]([N:18]1[CH2:23][CH2:22][CH:21]([CH:24]([OH:33])[CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=2[F:32])[CH2:20][CH2:19]1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(N(CC)CC)C>ClCCl.O>[CH2:11]([N:18]1[CH2:23][CH2:22][CH:21]([C:24](=[O:33])[CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=2[F:32])[CH2:20][CH2:19]1)[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

참가 물질

7

반응물 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 222481731-(1-Benzylpiperidin-4-yl)-2-(2-fluorophenyl)ethanol

생성물 1

HCID 222479931-(1-Benzylpiperidin-4-yl)-2-(2-fluorophenyl)ethanone수율 73%

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매3회

반응 조건

온도
-78 °C

실험 절차

After dissolving 7.5 ml of oxalyl chloride in 130 ml of dichloromethane, the solution was cooled to −78° C. and a solution of 6.1 ml of dimethylsulfoxide in dichloromethane (20 ml) was added dropwise while stirring. After stirring for 20 minutes, a solution of 13.4 g of 1-(1-benzylpiperidin-4-yl)-2-(2-fluorophenyl)ethanol in dichloromethane (40 ml) was added dropwise. After stirring for 30 minutes, 24 ml of triethylamine was added and the temperature was raised to room temperature. Water was added to the reaction solution, the organic layer was washed with water and saturated brine in that order and dried over anhydrous magnesium sulfate, and then the solvent was distilled off under reduced pressure. The residue was purified by NH silica gel column chromatography (solvent: n-hexane/ethyl acetate) to obtain the title compound (9.64 g, 73% yield).

후처리

  1. stirringAfter stirring for 20 minutes
  2. stirringAfter stirring for 30 minutes
  3. temperaturethe temperature was raised to room temperature
  4. washthe organic layer was washed with water and saturated brine in that order
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationthe solvent was distilled off under reduced pressure
  7. customThe residue was purified by NH silica gel column chromatography (solvent: n-hexane/ethyl acetate)

출처 및 근거

ORD 기록
ord-722ea4779f1247ca9b73bbff3e9331fa
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07915274B2

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