Benzyl Bromide → N-benzyl-7-bromo-1,2,3,4-tetrahydroquinoline
Reaction equation
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][CH2:8][NH:9]2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:18](Br)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>CN(C=O)C>[CH2:18]([N:9]1[C:10]2[C:5](=[CH:4][CH:3]=[C:2]([Br:1])[CH:11]=2)[CH2:6][CH2:7][CH2:8]1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 60 °C
Procedure
To a stirred solution of 7-bromo-1,2,3,4-tetrahydroquinoline (7.0 g, 33.0 mmol) in DMF (50 mL) was added potassium carbonate (13.6 g, 99.0 mmol), and benzyl bromide (4.33 mL, 36.3 mmol), and the mixture was heated to 60° C. for 12 h, then cooled to room temperature and quenched by the addition of ice-cold water (150 mL). The resulting mixture was extracted with ethyl acetate (3×50 mL), and the organic layers were combined and washed with water (50 mL) and brine (50 mL), then dried over sodium sulfate, concentrated and purified by silica gel column chromatography to furnish 1-benzyl-7-bromo-1,2,3,4-tetrahydro-quinoline (7.1 g).
Workup
- temperaturecooled to room temperature
- customquenched by the addition of ice-cold water (150 mL)
- extractionThe resulting mixture was extracted with ethyl acetate (3×50 mL)
- washwashed with water (50 mL) and brine (50 mL)
- dry with materialdried over sodium sulfate
- concentrationconcentrated
- custompurified by silica gel column chromatography
Sources & evidence
- ORD record
- ord-06cc487a1729405b8693c02686b23b19
- Source dataset
- uspto-grants-2013_06
- Patent number
- US08466114B2
Reaction notes
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