Trifluoroacetic acid → 1-(2-(5-Amino-2-(4-fluoro-phenoxy)-4-nitro-phenyl)-piperidin-1-yl)-ethanone

반응식

[N+:1]([O-:4])([O-])=[O:2].[K+].FC(F)(F)C(O)=O.[NH2:13][C:14]1[CH:15]=[CH:16][C:17]([O:29][C:30]2[CH:35]=[CH:34][C:33]([F:36])=[CH:32][CH:31]=2)=[C:18]([CH:20]2[CH2:25][CH2:24][CH2:23][CH2:22][N:21]2[C:26](=[O:28])[CH3:27])[CH:19]=1.C(=O)(O)[O-].[Na+]>>[NH2:13][C:14]1[C:15]([N+:1]([O-:4])=[O:2])=[CH:16][C:17]([O:29][C:30]2[CH:31]=[CH:32][C:33]([F:36])=[CH:34][CH:35]=2)=[C:18]([CH:20]2[CH2:25][CH2:24][CH2:23][CH2:22][N:21]2[C:26](=[O:28])[CH3:27])[CH:19]=1

참가 물질

반응물 4

HCID 6422Trifluoroacetic acid

HCID 24434Potassium Nitrate

HCID 516892Sodium Bicarbonate

HCID 231451501-(2-(5-Amino-2-(4-fluoro-phenoxy)-phenyl)-piperidin-1-yl)-ethanone

생성물 1

HCID 231454081-(2-(5-Amino-2-(4-fluoro-phenoxy)-4-nitro-phenyl)-piperidin-1-yl)-ethanone

실험 절차

64 mg of potassium nitrate was added to a trifluoroacetic acid (1 ml) solution of 190 mg of 1-(2-(5-amino-2-(4-fluoro-phenoxy)-phenyl)-piperidin-1-yl)-ethanone, and the reaction liquid was stirred overnight at room temperature. Aqueous saturated sodium bicarbonate was added to the reaction liquid to neutralize it, and then extracted with ethyl acetate. The organic layer was washed with saturated saline, and dried with anhydrous sodium sulfate. The solvent was evaporated away under reduced pressure, and the resulting residue was purified through silica gel column chromatography (developing solvent: hexane/ethyl acetate=1/1) to obtain the entitled compound as a yellow solid.