Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | 2-Piperidone | HCID 12665 | — |
| Reactant | N-benzyl-2-chloropyridine-4-carboxamide | HCID 15115857 | — |
| Reactant | Sodium t-butoxide | HCID 23676156 | — |
| Catalyst | palladium(II) acetate | HCID 167845 | — |
| Catalyst | Ferrocene-1,1'-bis-(diphenylphosphine) | HCID 635956 | — |
| Solvent | Toluene | HCID 1140 | — |
| Product | HCID 58247780 | HCID 58247780 | 21.2% |
Reaction Steps
A mixture of N-benzyl-2-chloroisonicotinamide (0.30 g, 1.22 mmol), piperidin-2-one (0.12 g, 1.22 mmol), 1,1′-bis(diphenylphosphino)ferrocene (0.03 g, 0.05 mmol), palladium acetate (0.01 g, 0.05 mmol) and sodium tert-butoxide (0.12 g, 1.22 mmol) in toluene (10 mL) was heated at 130° C. for 36 hours under nitrogen atmosphere and concentrated in vacuo to dryness. The residue was dissolved in dichloromethane (50 mL) and washed with water (30 mL). The separated organic solution was dried over anhydrous sodium sulphate, filtered and concentrated in vacuo. The residue was purified by column chromatography and eluted with 65-75% ethyl acetate in petroleum ether to give N-benzyl-2-(2-oxopiperidin-1-yl)isonicotinamide as a colorless solid (0.08 g, 21%): MS (ES+) m/z 310.1 (M+1).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09187426B2 |
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| Source dataset | uspto-grants-2015_11 |
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| ORD ID | ord-5650f70133d549a99796b96f912482c0 |
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| Source note | uspto-grants-2015_11 |
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