Water → 2-[N-methyl-(4-trifluoromethoxyphenyl)-amino]ethanol
Reaction equation
[CH3:1][NH:2][C:3]1[CH:8]=[CH:7][C:6]([O:9][C:10]([F:13])([F:12])[F:11])=[CH:5][CH:4]=1.Br[CH2:15][CH2:16][O:17]C1CCCCO1.C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[CH3:1][N:2]([C:3]1[CH:8]=[CH:7][C:6]([O:9][C:10]([F:11])([F:12])[F:13])=[CH:5][CH:4]=1)[CH2:15][CH2:16][OH:17]Participants
6
Conditions
- Temperature
- 100 °C
Procedure
A mixture of N-methyl-(4-trifluoromethoxyphenyl)amine (4.83 g, 24.24 mmol), 2-(2-bromoethoxy)-tetrahydropyran (6.1 g, 29.03 mmol), and potassium carbonate (3.84 g, 27.76 mmol) in DMF (20 ml) was stirred at 100° C. for 5 hours. The reaction mixture was allowed to return to room temperature, poured into water, and extracted with ethyl acetate twice. The extract was washed with water twice and brine, and dried over magnesium sulfate. After filtration, the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (methylene chloride/ethyl acetate=20/1) to afford 2-[N-methyl-(4-trifluoromethoxyphenyl)-amino]ethanol (3.1 g, yield 53%) as a pale yellow oil.
Workup
- customto return to room temperature
- extractionextracted with ethyl acetate twice
- washThe extract was washed with water twice
- dry with materialbrine, and dried over magnesium sulfate
- filtrationAfter filtration
- concentrationthe filtrate was concentrated under reduced pressure
- customThe residue was purified by silica gel column chromatography (methylene chloride/ethyl acetate=20/1)
Sources & evidence
- ORD record
- ord-073843149b46452298e48ccbed9587f2
- Source dataset
- uspto-grants-2007_08
- Patent number
- US07262212B2
Reaction notes
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