Water → 1,1-Dimethylethyl 4-azido-1-piperidinecarboxylate
Reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11](Br)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[N-:15]=[N+:16]=[N-:17].[Na+].O>CN(C)C=O>[N:15]([CH:11]1[CH2:12][CH2:13][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH2:9][CH2:10]1)=[N+:16]=[N-:17]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 60 °C
Procedure
To a solution of N-t butyloxycarbonyl-4-bromopiperidine (8.8 g, 33.5 mmol) in N,N-dimethylformamide (50 ml) was added sodium azide (6.5 g, 100.4 mmol) and the reaction mixture was heated at 60° C. for 18 hrs., cooled to room temperature, poured into water (200 ml) and extracted with dichloromethane (2×200 ml). The combined organic layers were washed with brine (2×50 ml), dried (MgSO4), filtered and concentrated under vacuum, to give the required product (6.0 g). 1H NMR (CDCl3) δ 1.28 (9H, s), 1.56 (2H,m), 1.88 (2H,m), 3.10 (2H,m), 3.58 (1H,m), 3.82 (2H,m).
Workup
- temperature, cooled to room temperature
- extractionextracted with dichloromethane (2×200 ml)
- washThe combined organic layers were washed with brine (2×50 ml)
- dry with materialdried (MgSO4)
- filtrationfiltered
- concentrationconcentrated under vacuum
Sources & evidence
- ORD record
- ord-a754f56e3432475d96d9e6c70a8ba7cf
- Source dataset
- uspto-grants-1999_08
- Patent number
- US05939436
Reaction notes
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