Tert-butyl 4-(2-bromo-4-nitrophenoxy)piperidine-1-carboxylate → Tert-butyl 4-(4-amino-2-bromophenoxy)piperidine-1-carboxylate
Reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([N+:22]([O-])=O)[CH:5]=[CH:6][C:7]=1[O:8][CH:9]1[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11][CH2:10]1>C(O)(=O)C.[Zn]>[Br:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][C:7]=1[O:8][CH:9]1[CH2:10][CH2:11][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:13][CH2:14]1)[NH2:22]Participants
4
Procedure
To a solution of 3-bromo-4-(1-t-butoxycarbonylpiperidin-4-yloxy)nitrobenzene (3.1 g) in acetic acid (40 ml) was added zinc powder (10.0 g) in ten portions and the mixture was stirred at room temperature for 5 hours. The reaction mixture was filtered through Celite (trade mark) and the filtrate was extracted with ethyl acetate. The extractant was washed with saturated aqueous potassium carbonate, water and brine, dried over anhydrous magnesium sulfate, filtered and the filtrate concentrated in vacuo. The residue was purified by chromatography on a silica gel column using hexane/ethyl acetate=1/1 as an eluant to give the desired compound (2.0 g, yield 69%) as a brown amorphous solid.
Workup
- filtrationThe reaction mixture was filtered through Celite (trade mark)
- extractionthe filtrate was extracted with ethyl acetate
- washThe extractant was washed with saturated aqueous potassium carbonate, water and brine
- dry with materialdried over anhydrous magnesium sulfate
- filtrationfiltered
- concentrationthe filtrate concentrated in vacuo
- customThe residue was purified by chromatography on a silica gel column
Sources & evidence
- ORD record
- ord-8f1e2f9bb5ed4f91880dc775dd20700e
- Source dataset
- uspto-grants-2003_04
- Patent number
- US06555556B1
Reaction notes
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