Methyl iodide → 4-Methyl-2-[2-(4-phenylbutyl)phenoxymethyl]morpholine
Reaction equation
C(=O)([O-])[O-].[K+].[K+].CI.C(O[C:14]([N:16]1[CH2:21][CH2:20][O:19][CH:18]([CH2:22][O:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[CH2:30][CH2:31][CH2:32][CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[CH2:17]1)=O)(C)(C)C>CC(N(C)C)=O>[CH3:14][N:16]1[CH2:21][CH2:20][O:19][CH:18]([CH2:22][O:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[CH2:30][CH2:31][CH2:32][CH2:33][C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=2)[CH2:17]1Participants
Procedure
115 mg of potassium carbonate and 118 mg of methyl iodide were added to a solution of 300 mg of 2-[2-(4-phenylbutyl)phenoxymethyl]morpholine hydrochloride (prepared as described in Example 7) in 6 ml of dimethylacetamide, and the resulting mixture was allowed to react at room temperature for 3 hours. At the end of this time, the reaction mixture was partitioned between ethyl acetate and water. The organic layer was washed with a saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate and concentrated by evaporation under reduced pressure. The resulting yellow oily residue was purified by column chromatography through silica gel, using ethyl acetate as the eluent, to give 183 mg (yield 65%) of the title compound as a colorless oil.
Workup
- customto react at room temperature for 3 hours
- customAt the end of this time, the reaction mixture was partitioned between ethyl acetate and water
- washThe organic layer was washed with a saturated aqueous solution of sodium chloride
- dry with materialdried over anhydrous magnesium sulfate
- concentrationconcentrated by evaporation under reduced pressure
- customThe resulting yellow oily residue was purified by column chromatography through silica gel
Sources & evidence
- ORD record
- ord-3cb7bf77cebc478abf0a594f12b794e2
- Source dataset
- uspto-grants-1996_09
- Patent number
- US05556864
Reaction notes
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