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

HRID 1025403Notes

Reaction equation

HRID 1025403 reaction equation
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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

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%).

Workup

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

Sources & evidence

ORD record
ord-82b9dc29de6a49b2897e37e278191044
Source dataset
uspto-grants-2014_05
Patent number
US08729081B2

Reaction notes

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