Methylamine → 2-(2-Fluorophenyl)ethylamine
Reaction equation
[CH3:1][NH2:2].[F:3][C:4]1[CH:11]=[CH:10][CH:9]=[CH:8][C:5]=1[CH2:6]Br>O1CCCC1.C(OCC)(=O)C>[F:3][C:4]1[CH:11]=[CH:10][CH:9]=[CH:8][C:5]=1[CH2:6][CH2:1][NH2:2]Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Procedure
To tetrahydrofuran (5 ml) was added under ice-cooling with stirring 40% aqueous methylamine solution (5 ml) and 2-fluorobenzylbromide (1.00 g, 5.29 mmol) dissolved in tetrahydrofuran (2 ml), and the mixture was stirred at the same temperature for 1 hr. The reaction mixture was diluted with ethyl acetate, and the organic layer was washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The insoluble material was filtered off, and the solution was concentrated under reduced pressure. The obtained oil was purified by silica gel column chromatography to give the title compound (0.65 g, yield 87%) as a colorless oil.
Workup
- temperaturecooling
- washthe organic layer was washed with water and saturated brine
- dry with materialdried over anhydrous magnesium sulfate
- filtrationThe insoluble material was filtered off
- concentrationthe solution was concentrated under reduced pressure
- customThe obtained oil was purified by silica gel column chromatography
Sources & evidence
- ORD record
- ord-9969e9fdd54f455aa2b960eecb90dd36
- Source dataset
- uspto-grants-2013_08
- Patent number
- US08513235B2
Reaction notes
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