Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Formaldehyde | HCID 712 | — |
| Reactant | Sodium Hydroxide | HCID 14798 | — |
| Reactant | Fumaric Acid | HCID 444972 | — |
| Reactant | HCID 13039291 | HCID 13039291 | — |
| Solvent | Formic Acid | HCID 284 | — |
| Solvent | Ethanol | HCID 702 | — |
| Solvent | Diethyl Ether | HCID 3283 | — |
| Product | HCID 86738228 | HCID 86738228 | — |
Reaction Steps
A mixture of 2.4 g of cis-4-(4-bromophenoxy)-3-phenylpiperidine, 7.2 ml of 100% formic acid and 0.81 ml of 37% aqueous formaldehyde solution is refluxed for one hour under nitrogen, cooled and made basic with 35 ml of 10% aqueous sodium hydroxide solution. The mixture is extracted with ether (2×50 ml), the ether extracts are washed with saturated sodium chloride solution, dried overnight over anhydrous sodium sulfate, filtered and concentrated in vacuo to afford a yellow oil. The oil is dissolved in 50 ml of ether and treated dropwise with stirring with a solution of 0.89 g of fumaric acid in a mixture of 75 ml of ether and 15 ml of absolute ethanol. The colorless, fine crystals which precipitate are filtered, washed with ether and dried to afford solid product, mp 172° C. dec.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US04312876 |
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| Source dataset | uspto-grants-1982_01 |
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| ORD ID | ord-2597d6436eb64fe48796243f9c0a907d |
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| Source note | uspto-grants-1982_01 |
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