Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Potassium Iodide | HCID 4875 | — |
| Reactant | Fumaric Acid | HCID 444972 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | 4-(3-Chloropropoxy)-3-methoxyacetophenone | HCID 7314264 | — |
| Reactant | HCID 15093838 | HCID 15093838 | — |
| Solvent | 1-Butanol | HCID 263 | — |
| Solvent | Methanol | HCID 887 | — |
| Solvent | Diethyl Ether | HCID 3283 | — |
| Product | HCID 23036358 | HCID 23036358 | 15.1% |
Reaction Steps
A mixture of 5.32 g (0.019 mole) of 4-[bis(3-fluorophenyl)methyl]piperidine, 4.80 g (0.020 mole) of 3-(4-acetyl-2-methoxyphenoxy)-1-chloropropane, 2.4 g (0.029 mole) of sodium bicarbonate and 0.20 g (0.0012) mole of potassium iodide in 400 ml of 1-butanol was heated at reflux for 23 hr. The solvent was removed in vacuo and the residue was partitioned between methylene chloride and dilute sodium hydroxide. The methylene chloride solution was dried over magnesium sulfate and the solvent was removed in vacuo to give an oil. This was dissolved in methanol and the solution was treated with an excess of fumaric acid. Ether was added and a gum formed. The gum was triturated with acetonitrile to give 1.75 g (15.1%) of the title compound as a white crystalline solid, mp 180°-181° C.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US04950674 |
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| Source dataset | uspto-grants-1990_08 |
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| ORD ID | ord-42135b1d2c01456aa88da38a7bf43c3d |
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| Source note | uspto-grants-1990_08 |
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