Sodium Bicarbonate → 1-[1-(4-Nitrophenyl)piperidin-4-yl]-4-(oxetan-3-yl)piperazine
Reaction equation
Cl.[N+:2]([C:5]1[CH:10]=[CH:9][C:8]([N:11]2[CH2:16][CH2:15][CH:14]([N:17]3[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]3)[CH2:13][CH2:12]2)=[CH:7][CH:6]=1)([O-:4])=[O:3].[O:23]1[CH2:26][C:25](=O)[CH2:24]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])O.[Na+]>C(Cl)(Cl)Cl.C(O)(=O)C.ClCCl>[N+:2]([C:5]1[CH:6]=[CH:7][C:8]([N:11]2[CH2:12][CH2:13][CH:14]([N:17]3[CH2:22][CH2:21][N:20]([CH:25]4[CH2:26][O:23][CH2:24]4)[CH2:19][CH2:18]3)[CH2:15][CH2:16]2)=[CH:9][CH:10]=1)([O-:4])=[O:3]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 3
Procedure
A mixture of 1-[1-(4-nitrophenyl)piperidin-4-yl]piperazine monohydrochloride (1 g), oxetan-3-one (300 mg), sodium triacetoxyborohydride (1.02 g), dichloromethane (20 mL), acetic acid (1 mL), and chloroform (30 mL) was stirred at room temperature for 2 days. To the reactant were added a saturated aqueous sodium hydrogen carbonate solution and chloroform, followed by liquid separation. The organic phase was washed with saturated brine and dried over anhydrous magnesium sulfate, and then the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (eluent; chloroform:methanol=1:0-9:1) to obtain 1-[1-(4-nitrophenyl)piperidin-4-yl]-4-(oxetan-3-yl)piperazine (670 mg) as a yellow solid.
Workup
- customfollowed by liquid separation
- washThe organic phase was washed with saturated brine
- dry with materialdried over anhydrous magnesium sulfate
- customthe solvent was evaporated under reduced pressure
- customThe obtained residue was purified by silica gel column chromatography (eluent; chloroform:methanol=1:0-9:1)
Sources & evidence
- ORD record
- ord-a8800b6858194b22ae0b926a14ade9cb
- Source dataset
- uspto-grants-2015_07
- Patent number
- US09085540B2
Reaction notes
Loading…