Potassium Carbonate → HCID 178501112, compound

HRID 538054Notes

Reaction equation

C([O-])([O-])=O.[K+].[K+].F[C:8]1[CH:13]=[C:12]([C:14]([F:17])([F:16])[F:15])[CH:11]=[CH:10][C:9]=1[N+:18]([O-:20])=[O:19].[CH3:21][O:22][C:23]([C@H:25]1[CH2:30][CH2:29][C@H:28]([CH2:31][NH2:32])[CH2:27][CH2:26]1)=[O:24]>CN(C=O)C>[CH3:21][O:22][C:23]([C@H:25]1[CH2:30][CH2:29][C@H:28]([CH2:31][NH:32][C:8]2[CH:13]=[C:12]([C:14]([F:17])([F:16])[F:15])[CH:11]=[CH:10][C:9]=2[N+:18]([O-:20])=[O:19])[CH2:27][CH2:26]1)=[O:24]

Participants

Conditions

Temperature: 50 °C

Procedure

K2CO3 (1.6 g, 11.7 mmol), 2-Fluoro-1-nitro-4-trifluoromethyl-benzene (1.22 g, 5.8 mmol) and trans-4-Aminomethyl-cyclohexanecarboxylic acid methyl ester (1.00 g, 5.84 mmol) were dissolved in DMF (10 ml). The mixture was stirred at 50° C. overnight. The solvent was removed under reduced pressure and the crude product dissolved in DCM (15 ml) and washed with water (20 ml) and then with a solution of citric acid (1M, 5 ml). The organic solution was dried over Na2SO4, filtered and the solvent removed by evaporation to give solid material. This was washed with cyclohexane and then with isopropyl ether and purified by silica column using DCM/cyclo hexane (1:1) as eluent. 1.8 g (yield 86%) of the title compound were isolated.

Workup

customThe solvent was removed under reduced pressure
dissolutionthe crude product dissolved in DCM (15 ml)
washwashed with water (20 ml)
dry with materialThe organic solution was dried over Na2SO4
filtrationfiltered
customthe solvent removed by evaporation
customto give solid material
washThis was washed with cyclohexane
customwith isopropyl ether and purified by silica column

Sources & evidence

ORD record: ord-2d482fafe8e649b8841a8f7e5390fded
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08865704B2

Reaction notes

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