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

HRID 914808

反応式

HRID 914808 の反応式
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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒3 回

反応条件

温度
-78 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-319b5e2b99ed41ca846a55bd1ae62ef4
出典データセット
uspto-grants-2007_09
特許番号
US07265108B2

関連ノート

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