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

HRID 914811Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 914811
C(Cl)(=O)C(Cl)=O.CS(C)=O.[CH2:11]([N:18]1[CH2:23][CH2:22][CH:21]([CH2:24][CH:25]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[Cl:33])[OH:26])[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.C(OCC)(=O)C.O>[CH2:11]([N:18]1[CH2:19][CH2:20][CH:21]([CH2:24][C:25]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[Cl:33])=[O:26])[CH2:22][CH2:23]1)[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Komponenten

8

Edukt 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 222485842-(1-Benzylpiperidin-4-yl)-1-(2-chlorophenyl)ethanol

Produkt 1

HCID 222478472-(1-Benzylpiperidin-4-yl)-1-(2-chlorophenyl)ethanoneAusbeute 47 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel3×HCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

After dissolving 1.30 ml of oxalyl chloride in 30 ml of dichloromethane, the solution was cooled to −78° C., and a solution of 1.22 ml of dimethylsulfoxide in dichloromethane (5 ml) was added dropwise while stirring. The mixture was stirred for 3 minutes, and then a solution of 2-(1-benzylpiperidin-4-yl)-1-(2-chlorophenyl)ethanol in dichloromethane (10 ml) was added dropwise. After stirring for 30 minutes, 8.01 ml of triethylamine was added, the temperature was raised to room temperature and stirring was continued for 3 hours. Water was added to the reaction solution, and extraction was performed with ethyl acetate. 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 (1.78 g, 47% yield, 2 steps).

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-fbfbbfe3f13d4172999fbf4dc7babe52
Quelldatensatz
uspto-grants-2007_09
Patentnummer
US07265108B2

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