Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | 2-Vinylpyridine | HCID 7521 | — |
| Reactant | Sodium Hydroxide | HCID 14798 | — |
| Reactant | 1,2,3,4,5,6-Hexahydro-3,9-dimethylazepino[4,5-b]indole | HCID 68560092 | — |
| Solvent | Water | HCID 962 | — |
| Product | HCID 59368249 | HCID 59368249 | 35.8% |
Reaction Steps
The title compound was prepared by following general procedure 4. To a solution of 3,9-dimethyl-1,2,3,4,5,6-hexahydroazepino[4,5-b]indole (150 mg, 0.7 mmol) in 50% aq. NaOH solution (7 mL) tetra n-butyl ammonium chloride (9 mg, 0.03 mmol) followed by 2-vinylpyridine (80 mg, 0.77 mmol) was added and the reaction mixture was heated at 80° C. for 14 h. After completion of reaction, the reaction mixture was diluted with water, extracted with ethyl acetate; the organic layer was dried over Na2SO4, and concentrated under reduced pressure. The crude product was purified by reverse phase chromatography to afford 80 mg of 3,9-dimethyl-6-(2-(pyridin-2-yl)ethyl)-1,2,3,4,5,6-hexahydroazepino[4,5-b]indole as the TFA salt.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08569287B2 |
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| Source dataset | uspto-grants-2013_10 |
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| ORD ID | ord-2c370214ec614da4b46e3b1991c4004a |
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| Source note | uspto-grants-2013_10 |
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