Potassium Carbonate → Ethyl 1-((2-(4-chlorophenyl)-5-methyloxazol-4-yl)methyl)piperidine-4-carboxylate

HRID 1025403

Reaktionsgleichung

Reaktionsgleichung von HRID 1025403
Cl[CH2:2][C:3]1[N:4]=[C:5]([C:9]2[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][CH:10]=2)[O:6][C:7]=1[CH3:8].[NH:16]1[CH2:21][CH2:20][CH:19]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH2:18][CH2:17]1.C([O-])([O-])=O.[K+].[K+]>O1CCOCC1>[Cl:15][C:12]1[CH:13]=[CH:14][C:9]([C:5]2[O:6][C:7]([CH3:8])=[C:3]([CH2:2][N:16]3[CH2:21][CH2:20][CH:19]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH2:18][CH2:17]3)[N:4]=2)=[CH:10][CH:11]=1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 70770Ethyl 4-piperidinecarboxylateHCID 36136584-(Chloromethyl)-2-(4-chlorophenyl)-5-methyl-1,3-oxazole

Produkt 1

HCID 42116034Ethyl 1-((2-(4-chlorophenyl)-5-methyloxazol-4-yl)methyl)piperidine-4-carboxylateAusbeute 91 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

The mixture of 4-(chloromethyl)-2-(4-chlorophenyl)-5-methyloxazole (1.21 g, 5 mmole, commercially from Fluorochem) and ethyl piperidine-4-carboxylate (0.81 mL, 1.05 equiv.), K2CO3 (1.03 g, 1.5 equiv) in dioxane was stirred at 70° C. for 2 h. The reaction solution was cooled to room temperature and the solid was filtered off, rinsed with dichloromethane. The filtrate was concentrated and the residue was recrystallized from hexane to furnish Ethyl 1-((2-(4-chlorophenyl)-5-methyloxazol-4-yl)methyl)piperidine-4-carboxylate (1.65 g, 91%).

Aufarbeitung

  1. filtrationthe solid was filtered off
  2. washrinsed with dichloromethane
  3. concentrationThe filtrate was concentrated
  4. customthe residue was recrystallized from hexane

Quellen und Nachweise

ORD-Eintrag
ord-82b9dc29de6a49b2897e37e278191044
Quelldatensatz
uspto-grants-2014_05
Patentnummer
US08729081B2

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