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
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
1-Benzylpiperidin-4-ylamine (3 g, 15.8 mmol) 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. 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. The organic layer was separated, 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 subjected to a silica gel column chromatography to obtain 3.80 g of the title compound as a white solid (yield 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
- customThe organic layer was separated
- washwashed 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
Sources & evidence
- ORD record
- ord-040d32411aa241908b09b492c50f7232
- Source dataset
- uspto-grants-2011_11
- Patent number
- US08053435B2
Reaction notes
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