Ethanol → 4-(Ethoxycarbonylamino)-1-[[2-(3,4,5-trimethoxyphenyl)pyridin-4-yl]methyl]piperidine
Reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:13]2[CH:18]=[C:17]([CH2:19][N:20]3[CH2:25][CH2:24][CH:23](C(N)=O)[CH2:22][CH2:21]3)[CH:16]=[CH:15][N:14]=2)[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9][CH3:10].[CH2:29]([OH:31])[CH3:30].FC(F)(F)C(OI(C1C=CC=CC=1)O[C:39](=[O:44])C(F)(F)F)=O.C(#[N:55])C>>[CH2:29]([O:31][C:39]([NH:55][CH:23]1[CH2:24][CH2:25][N:20]([CH2:19][C:17]2[CH:16]=[CH:15][N:14]=[C:13]([C:5]3[CH:4]=[C:3]([O:2][CH3:1])[C:8]([O:9][CH3:10])=[C:7]([O:11][CH3:12])[CH:6]=3)[CH:18]=2)[CH2:21][CH2:22]1)=[O:44])[CH3:30]Participants
5
Procedure
To a solution of 1-[[2-(3,4,5-trimethoxyphenyl)pyridin-4-yl]methyl]piperidine-4-carboxamide (528 mg) in a mixed solvent of ethanol (10 mL) and acetonitrile (10 mL) was added [bis(trifluoroacetoxy)iodo]benzene (884 mg). The mixture was stirred at room temperature overnight and evaporated. Saturated aqueous sodium hydrogen carbonate was added to the residue and extracted with chloroform. The organic layer was washed with brine, dried over anhydrous magnesium sulfate and evaporated. The residue was applied to a column of silica gel and purified using chloroform-methanol (20:1) as an eluent to give the title compound.
Workup
- customevaporated
- additionSaturated aqueous sodium hydrogen carbonate was added to the residue
- extractionextracted with chloroform
- washThe organic layer was washed with brine
- dry with materialdried over anhydrous magnesium sulfate
- customevaporated
- custompurified
Sources & evidence
- ORD record
- ord-ec18a909af2943c1bfc5cc656d06b213
- Source dataset
- uspto-grants-2003_08
- Patent number
- US06605620B1
Reaction notes
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