Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Dibromomethane | HCID 3024 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | HCID 22004789 | HCID 22004789 | — |
| Catalyst | Copper oxide | HCID 14829 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 22004788 | HCID 22004788 | 67% |
Reaction Steps
A solution of N-[2-(6,7-dihydroxyindan-1-yl)ethyl]butyramide (1.13 g, 4.29 mmol.), dibromomethane (2.98 g, 17.2 mmol.), potassium carbonate (1.78 g, 12.9 mmol.) and copper-(II) oxide (34 mg, 0.43 mmol.) in N,N-dimethylformamide (15 mL) was stirred for 3 hours at 110° C. The reaction mixture was cooled, which was poured into water, followed by neutralizing with dilute hydrochloric acid. The organic matter was extracted with ethyl acetate. The extract solution was washed with a saturated aqueous saline solution and water, which was then dried over anhydrous magnesium sulfate, followed by distilling off the solvent under reduced pressure. The residue was purified by means of silica gel column chromatography (ethyl acetate) to afford the title compound (yield 785 mg, 67%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US06034239 |
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| Source dataset | uspto-grants-2000_03 |
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| ORD ID | ord-866d5ae17b9e410597402da8c9449403 |
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| Source note | uspto-grants-2000_03 |
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