Potassium Carbonate → 4-Methyl-1-{4-[5-(3-chloro-4-cyclohexylphenyl)-[1,2,4]-oxadiazol-3-yl]benzyl}piperidine-4-carboxylic acid ethyl ester

HRID 1777358Notes

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:32]2[O:36][N:35]=[C:34]([C:37]3[CH:42]=[CH:41][C:40]([CH2:43]Cl)=[CH:39][CH:38]=3)[N:33]=2)[CH:23]=[CH:24][C:25]=1[CH:26]1[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1>CN(C)C=O>[CH2:7]([O:9][C:10]([C:12]1([CH3:18])[CH2:17][CH2:16][N:15]([CH2:43][C:40]2[CH:39]=[CH:38][C:37]([C:34]3[N:33]=[C:32]([C:22]4[CH:23]=[CH:24][C:25]([CH:26]5[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]5)=[C:20]([Cl:19])[CH:21]=4)[O:36][N:35]=3)=[CH:42][CH:41]=2)[CH2:14][CH2:13]1)=[O:11])[CH3:8]

Participants

Conditions

Temperature: 67.5 °C

Procedure

Potassium carbonate (0.16 g, 0.0012 mol) and 4-methylpiperidine-4-carboxylic acid ethyl ester (0.21 g, 0.0012 mol) are added to a solution of 5-(3-chloro-4-cyclohexylphenyl)-3-(4-chloromethylphenyl)-[1,2,4]-oxadiazole (0.3 g, 0.00077 mol) in N,N-dimethylformamide 15 mL). The reaction mixture is heated at 65-70° C. for 2 hrs. Removal of solvent gives a crude residue which is purified by column chromatography (silica gel 230-400 mesh, ethyl acetate:toluene, 1:4) to give 4-methyl-1-{4-[5-(3-chloro-4-cyclohexylphenyl)-[1,2,4]-oxadiazol-3-yl]benzyl}piperidine-4-carboxylic acid ethyl ester.

Workup

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

Sources & evidence

ORD record: ord-c2aeba9ccca448e4822a33b4ebf3b7e3
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09266867B2

Reaction notes

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