Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | 1-Iodopropane | HCID 33643 | — |
| Reactant | HCID 57445555 | HCID 57445555 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Product | HCID 16046080 | HCID 16046080 | 46.5% |
Reaction Steps
To a solution of 4-[3-fluoro-5-(methylsulfonyl)phenyl]piperidine (0.5 g, 1.94 mmol) in acetonitrile (5 ml) was added potassium carbonate (0.53 g, 3.83 mmol) and 1-iodopropane (0.189 ml, 1.94 mmol) and the mixture was heated with microwave irradiation for 20 min at 150° C. The mixture was cooled to ambient temperature and water (50 ml) was added. The aqueous residue was extracted with ethylacetate (3×50 ml) and the combined organic phases was dried, concentrated, and purified by flash column chromatography (ethylacetate/methanol, 1:1) to give the title compound (0.27 g, 46%). The amine was converted to the hydrochloric acid salt and recrystallized from ethanol/diethyl ether: M.p. 187-189° C. MS m/z (relative intensity, 70 eV) 299 (M+, 3), 271 (15), 270 (bp), 147 (5) 133 (5).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08501777B2 |
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| Source dataset | uspto-grants-2013_08 |
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| ORD ID | ord-5ac554114ef04c91bd0dad93b1080858 |
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| Source note | uspto-grants-2013_08 |
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