Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Piperidine | HCID 8082 | — |
| Reactant | Ethyl Acetate | HCID 8857 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | 2-chloro-N-(3-quinoxalin-2-ylphenyl)acetamide | HCID 1485433 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Product | HCID 46916365 | HCID 46916365 | 43% |
Reaction Steps
To a slurry of 2-chloro-N-(3-quinoxalin-2-ylphenyl)acetamide (100 mg, 0.336 mmol) and K2CO3 (56 mg, 0.403 mmol) in MeCN (5 mL), piperidine (35 μL, 0.353 mmol) was added and the reaction mixture was stirred at reflux for 18 hrs. The solvent was evaporated in vacuo and the residue was purified by flash chromatography (Flash Master, Isolute 5 g silica, gradient 0-5 min, 100% hexane and then 0-100% ethyl acetate over 40 min) to afford 2-(piperidin-1-yl)-N-[3-(quinoxalin-2-yl)phenyl]acetamide (50 mg, 42% yield). LCMS calculated for C21H22N4O (M+H): 347.18. found 347. 1H-NMR (DMSO-d6, 400 Mhz) δH: 9.88 (1H, br. s), 9.48 (1H, s), 8.54 (1H, m), 8.12-8.10 (2H, m), 7.98 (1H, d, J=7 Hz), 7.91-7.81 (3H, m), 7.52 (1H, m), 3.12 (2H, s), 2.55-2.53 (4H, m), 1.61-1.55 (4H, m), 1.42-1.36 (2H, m).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08592415B2 |
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| Source dataset | uspto-grants-2013_11 |
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| ORD ID | ord-b2add2e4212b40efaaf022faca4cf1d8 |
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| Source note | uspto-grants-2013_11 |
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