Diisopropylethylamine → Ethanamine, N-methyl-2-[3-(trifluoromethyl)phenoxy]-
Reaction equation
Cl.CN.C([N:7]([CH2:11]C)[CH:8]([CH3:10])C)(C)C.BrCC[O:16][C:17]1[CH:18]=[C:19]([C:23]([F:26])([F:25])[F:24])[CH:20]=[CH:21][CH:22]=1>O1CCCC1>[CH3:11][NH:7][CH2:8][CH2:10][O:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([C:23]([F:24])([F:25])[F:26])[CH:18]=1Participants
Procedure
A mixture of methylamine hydrochloride salt (380 mg, 5.57 mmol) in tetrahydrofuran (10 mL) was treated with N,N-diisopropylethylamine (1.44 g, 11.15 mmol) and 3-(2-bromoethoxy)benzotrifluoride (300 mg, 1.11 mmol). The reaction mixture was allowed to stir at reflux for 2 d. At this time, the reaction was quenched by the addition of water. The aqueous layer was extracted with ethyl acetate. The organics were washed with a saturated aqueous sodium chloride solution, dried over magnesium sulfate, filtered and concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 230-400 mesh, 95/5 methylene chloride/methanol) afforded methyl-[2-(3-trifluoromethyl-phenoxy)-ethyl]-amine (110 mg, 45%) as yellow solid. The NMR spectrum obtained on the sample is compatible with its structure.
Workup
- temperatureat reflux for 2 d
- customAt this time, the reaction was quenched by the addition of water
- extractionThe aqueous layer was extracted with ethyl acetate
- washThe organics were washed with a saturated aqueous sodium chloride solution
- dry with materialdried over magnesium sulfate
- filtrationfiltered
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-557e15ae6a3241529857cd679cc82151
- Source dataset
- uspto-grants-2011_05
- Patent number
- US07947692B2
Reaction notes
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