HCID 18537920, compound → 2-(2-Methoxyphenoxy)ethyl amine
Reaction equation
[CH3:1][O:2][C:3]1[CH:19]=[CH:18][CH:17]=[CH:16][C:4]=1[O:5][CH2:6][CH2:7][NH:8]C(=O)OC(C)(C)C>FC(F)(F)C(O)=O.ClCCl>[CH3:1][O:2][C:3]1[CH:19]=[CH:18][CH:17]=[CH:16][C:4]=1[O:5][CH2:6][CH2:7][NH2:8]Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 23 °C
Procedure
tert-Butyl 2-(2-methoxyphenoxy)ethylcarbamate (23.8 g, 89 mmol) was cooled to 0° C. and stirred as a mixture of trifluoroacetic acid:dichloromethane (1:1, 40 mL) was added dropwise. The mixture was allow to warm to 23° C., stirred for 2 hours and concentrated in vacuo. The residue was taken back up in dichloromethane (100 mL) and the solution was washed with saturated aqueous sodium hydrogen carbonate (3×20 mL) and aqueous sodium hydroxide (10%, 3×20 mL), dried (Na2SO4), filtered and concentrated in vacuo to provide 2-(2-methoxyphenoxy)ethylamine (13 g, 88% yield) a light yellow solid; MS (PB-PCI) C9H13NO2 m/e calc 167.21; found 168 (MH+).
Workup
- additionwas added dropwise
- concentrationconcentrated in vacuo
- washthe solution was washed with saturated aqueous sodium hydrogen carbonate (3×20 mL) and aqueous sodium hydroxide (10%, 3×20 mL)
- dry with materialdried (Na2SO4)
- filtrationfiltered
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-9620c0e52a324cc0b91675b00e34b2d8
- Source dataset
- uspto-grants-2003_05
- Patent number
- US06562854B2
Reaction notes
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