3-(Cyclohexen-1-yl)aniline → N-[3-(cyclohexen-1-yl)phenyl]-4-hydroxy-3-methoxyphenylacetamide

HRID 7062

Reaction equation

FC1C(O[C:9](=[O:20])[CH2:10][C:11]2[CH:16]=[CH:15][C:14]([OH:17])=[C:13]([O:18][CH3:19])[CH:12]=2)=C(F)C(F)=C(F)C=1F.[C:25]1([C:31]2[CH:32]=[C:33]([CH:35]=[CH:36][CH:37]=2)[NH2:34])[CH2:30][CH2:29][CH2:28][CH2:27][CH:26]=1>C(OCC)(=O)C>[C:25]1([C:31]2[CH:32]=[C:33]([NH:34][C:9](=[O:20])[CH2:10][C:11]3[CH:16]=[CH:15][C:14]([OH:17])=[C:13]([O:18][CH3:19])[CH:12]=3)[CH:35]=[CH:36][CH:37]=2)[CH2:30][CH2:29][CH2:28][CH2:27][CH:26]=1

Participants

Conditions

Temperature: 60 °C

Procedure

4-Hydroxy-3-methoxyphenylacetic acid pentafluorophenyl ester (60 mg) and Intermediate 2 (60 mg) are dissolved in ethyl acetate, and the mixture is stirred at 60° C. for 18 hours. The solvent is evaporated under reduced pressure, and the residue is purified by silica gel column chromatography (eluent: gradient from 0% to 100% hexane/ethyl acetate) to give the title compound (50 mg).

Workup

customThe solvent is evaporated under reduced pressure
customthe residue is purified by silica gel column chromatography (eluent: gradient from 0% to 100% hexane/ethyl acetate)

Sources & evidence

ORD record: ord-cd1c80ce4ddb43ffb41ba233536d3992
Source dataset: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07084176B2

Linked notes

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