Potassium Carbonate → 1-{4-[5-(3-Chloro-4-isobutylphenyl)-[1,2,4]-oxadiazol-3-yl]-benzyl}-4-methylpiperidine-4-carboxylic acid ethyl ester

HRID 1777362Notes

Reaction equation

C(=O)([O-])[O-].[K+].[K+].[CH2:7]([O:9][C:10]([C:12]1([CH3:18])[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1)=[O:11])[CH3:8].[Cl:19][C:20]1[CH:21]=[C:22]([C:30]2[O:34][N:33]=[C:32]([C:35]3[CH:40]=[CH:39][C:38]([CH2:41]Cl)=[CH:37][CH:36]=3)[N:31]=2)[CH:23]=[CH:24][C:25]=1[CH2:26][CH:27]([CH3:29])[CH3:28]>CN(C)C=O>[CH2:7]([O:9][C:10]([C:12]1([CH3:18])[CH2:17][CH2:16][N:15]([CH2:41][C:38]2[CH:37]=[CH:36][C:35]([C:32]3[N:31]=[C:30]([C:22]4[CH:23]=[CH:24][C:25]([CH2:26][CH:27]([CH3:28])[CH3:29])=[C:20]([Cl:19])[CH:21]=4)[O:34][N:33]=3)=[CH:40][CH:39]=2)[CH2:14][CH2:13]1)=[O:11])[CH3:8]

Participants

Conditions

Temperature: 67.5 °C

Procedure

Potassium carbonate (0.29 g, 0.0021 mol) and 4-methylpiperidine-4-carboxylic acid ethyl ester (0.36 g, 0.0021 mol) are added to a solution of 5-(3-chloro-4-isobutylphenyl)-3-(4-chloromethylphenyl)-[1,2,4]-oxadiazole (0.5 g, 0.0014 mol) in N,N-dimethylformamide (10 mL). The reaction mixture is heated at 65-70° C. for 2 hours. Removal of solvent gives a crude residue which is purified by column chromatography (silica gel 230-400 mesh, toluene:ethyl acetate 4:1) to give 1-{4-[5-(3-chloro-4-isobutylphenyl)-[1,2,4]-oxadiazol-3-yl]-benzyl}-4-methylpiperidine-4-carboxylic acid ethyl ester.

Workup

customRemoval of solvent
customgives a crude residue which
customis purified by column chromatography (silica gel 230-400 mesh, toluene:ethyl acetate 4:1)

Sources & evidence

ORD record: ord-fc8c392f678447b8b6d3e8314edb1c0d
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09266867B2

Reaction notes

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