Dimethyl Sulfoxide → 1-(4-Methylbenzyl)piperidin-4-one

HRID 49443

Reaktionsgleichung

Reaktionsgleichung von HRID 49443
C(Cl)(=O)C(Cl)=O.CS(C)=O.[CH3:11][C:12]1[CH:25]=[CH:24][C:15]([CH2:16][N:17]2[CH2:22][CH2:21][CH:20]([OH:23])[CH2:19][CH2:18]2)=[CH:14][CH:13]=1.C(N(CC)CC)C.[Cl-].[NH4+]>C(Cl)Cl>[CH3:11][C:12]1[CH:13]=[CH:14][C:15]([CH2:16][N:17]2[CH2:18][CH2:19][C:20](=[O:23])[CH2:21][CH2:22]2)=[CH:24][CH:25]=1

Komponenten

7

Edukt 5

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 65578Oxalyl chlorideHCID 7914821-(4-Methylbenzyl)piperidin-4-ol

Produkt 1

HCID 119595411-(4-Methylbenzyl)piperidin-4-oneAusbeute 81 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To 2.8 mL (32 mmol) of oxalyl chloride in 75 mL of CH2Cl2 at −78° C. was added 4.6 mL (64 mmol) of DMSO. To this mixture was added 5.3 g (26 mmol) of 1-(4-methylbenzyl)-4-piperidinol 123 in 10 mL of CH2Cl2, and the mixture was stirred 5 min in the cold. The mixture was quenched with 18 mL (129 mmol) of triethylamine and allowed to come to room temperature, and saturated aqueous ammonium chloride was added. The organic phase was washed with water and brine, dried, and evaporated to give 4.27 g (81%) of 1-(4-methylbenzyl)-4-piperidinone (124), which was used as is without further purification. GC/MS showed 100% purity with a molecular ion of 203.

Aufarbeitung

  1. customto come to room temperature
  2. washThe organic phase was washed with water and brine
  3. customdried
  4. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-fb7270a74cbc4031b8e83c2f70138da2
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06706740B2

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