Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrogen Bromide | HCID 260 | — |
| Reactant | Oxalic Acid | HCID 971 | — |
| Reactant | Arecoline | HCID 2230 | — |
| Reactant | Sodium ethoxide | HCID 2723922 | — |
| Reactant | N'-Hydroxy-2-methylpropanimidamide | HCID 2794833 | — |
| Solvent | Ethanol | HCID 702 | — |
| Product | HCID 23047524 | HCID 23047524 | 37% |
Reaction Steps
816 mg(8.0 mmol) of isopropylcarboxamide oxime was added to a solution of sodium ethoxide (7.8 mmol) in 20 ml of distilled ethanol and 5 g molecular sieves. The mixture was stirred at room temperature for 10 min whereafter 1.0 g(4.23 mmol) of arecoline, HBr was added. The mixture was heated at 80° C. for 12 hours, filtered, and evaporated in vacuo. 10 ml of water was added to the residue and the mixture was extracted with ether (3×50 ml). The combined extracts were dried with MgSO4 and evaporated in vacuo. The residue was dissolved in 5 ml of 99.9% ethanol and a solution of 380 mg(4.23 mmol) of oxalic acid in 10 ml of 99.9% ethanol was added. Crystallization from ether gave the title compound in 37% yield. M.P. 133°-134° C.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US04837241 |
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| Source dataset | uspto-grants-1989_06 |
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| ORD ID | ord-d3edd0729743435880784b5410672d0d |
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| Source note | uspto-grants-1989_06 |
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