Sodium Iodide → 1-[2-(Tetrahydropyran-2-yloxy)ethyl]-4-(4-trifluoromethylphenoxy)piperidine
Reaction equation
[F:1][C:2]([F:17])([F:16])[C:3]1[CH:15]=[CH:14][C:6]([O:7][CH:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)=[CH:5][CH:4]=1.Br[CH2:19][CH2:20][O:21][CH:22]1[CH2:27][CH2:26][CH2:25][CH2:24][O:23]1.C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>CN(C=O)C.O>[O:23]1[CH2:24][CH2:25][CH2:26][CH2:27][CH:22]1[O:21][CH2:20][CH2:19][N:11]1[CH2:10][CH2:9][CH:8]([O:7][C:6]2[CH:14]=[CH:15][C:3]([C:2]([F:1])([F:16])[F:17])=[CH:4][CH:5]=2)[CH2:13][CH2:12]1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 100 °C
Procedure
A mixture of 4-(4-trifluoromethylphenoxy)-piperidine (1.87 g, 7.63 mmol), 2-(2-bromoethoxy)-tetrahydropyran (1.75 g, 8.4 mmol), potassium carbonate (1.16 g, 8.38 mmol), sodium iodide (1.2 g, 8.01 mmol) in DMF (30 ml) was stirred at 100° C. for 1 hour. 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/methanol=50/1) to afford 1-[2-(tetrahydropyran-2-yloxy)ethyl]-4-(4-trifluoromethylphenoxy)piperidine (1.69 g, yield 59%) as a colorless 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/methanol=50/1)
Sources & evidence
- ORD record
- ord-5150eea560c240e2a9fbdc981192b314
- Source dataset
- uspto-grants-2007_08
- Patent number
- US07262212B2
Reaction notes
Loading…