Dimethyl Sulfoxide → (1-Benzylpiperidin-4-yl)-(1,3-dihydroisobenzofuran-1-yl)methanone

HRID 914856Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 914856
CS(C)=O.C(Cl)(=O)C(Cl)=O.[CH2:11]([N:18]1[CH2:23][CH2:22][CH:21]([CH:24]([CH:26]2[C:34]3[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=3)[CH2:28][O:27]2)[OH:25])[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>[CH2:11]([N:18]1[CH2:19][CH2:20][CH:21]([C:24]([CH:26]2[C:34]3[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=3)[CH2:28][O:27]2)=[O:25])[CH2:22][CH2:23]1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Komponenten

6

Edukt 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 22248465(1-Benzylpiperidin-4-yl)-(1,3-dihydroisobenzofuran-1-yl)methanol

Produkt 1

HCID 22248144(1-Benzylpiperidin-4-yl)-(1,3-dihydroisobenzofuran-1-yl)methanoneAusbeute 87,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

After adding 0.511 ml of dimethylsulfoxide dropwise to a dichloromethane solution (15 ml) containing 0.315 ml of oxalyl chloride at −70° C., the mixture was stirred for 10 minutes, a solution of 597 mg of (1-benzylpiperidin-4-yl)-(1,3-dihydroisobenzofuran-1-yl)methanol in dichloromethane (5 ml) was added dropwise, and stirring was continued for 1 hour. Next, 2.5 ml of triethylamine was added dropwise to the reaction solution, the cooling bath was removed, and the mixture was stirred at room temperature. Water was added to the reaction solution, and extraction was performed with ethyl acetate. After drying over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure to obtain the title compound (517 mg, 33% yield).

Aufarbeitung

  1. stirringstirring
  2. waitwas continued for 1 hour
  3. customthe cooling bath was removed
  4. stirringthe mixture was stirred at room temperature
  5. additionWater was added to the reaction solution, and extraction
  6. dry with materialAfter drying over anhydrous magnesium sulfate
  7. distillationthe solvent was distilled off under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-a3d861881ba347609a29246b82287887
Quelldatensatz
uspto-grants-2007_09
Patentnummer
US07265108B2

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