tert-Butanol → 1-Benzyl-4-(N-Boc-amino)piperidine
Reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([NH2:14])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)(C)(C)C.[C:20]([O:24][C:25](OC([O-])=O)=[O:26])([CH3:23])([CH3:22])[CH3:21]>[OH-].[Na+]>[C:20]([O:24][C:25](=[O:26])[NH:14][CH:11]1[CH2:12][CH2:13][N:8]([CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH2:9][CH2:10]1)([CH3:23])([CH3:22])[CH3:21]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
1-Benzylpiperidin-4-ylamine (3 g, 15.8 mmol), the starting material, was dissolved in 1M aqueous sodium hydroxide solution (35.8 ml) and t-butanol (32 ml) in a 250 ml vessel, and t-butyl-dicarbonate ((t-Boc)2O; 3.79 g, 17.38 mmol) was added thereto while stirring, and the resulting mixture was reacted at room temperature for 12 hrs. After the completion of reaction, the reaction mixture was extracted with ethyl acetate twice. Then, the organic layer was washed with 0.1N hydrochloric acid solution and brine in order, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue thus obtained was purified with a silica gel column chromatography to obtain 3.80 g of the title compound as a white solid (82.8%).
Workup
- customthe resulting mixture was reacted at room temperature for 12 hrs
- customAfter the completion of reaction
- extractionthe reaction mixture was extracted with ethyl acetate twice
- washThen, the organic layer was washed with 0.1N hydrochloric acid solution and brine in order
- dry with materialdried over anhydrous sodium sulfate
- filtrationfiltered
- concentrationconcentrated under reduced pressure
- customThe residue thus obtained
- customwas purified with a silica gel column chromatography
Sources & evidence
- ORD record
- ord-1bc73f53efec4300b220744484a65aea
- Source dataset
- uspto-grants-2011_11
- Patent number
- US08053435B2
Reaction notes
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