Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Piperidine | HCID 8082 | — |
| Reactant | tert-Butyl cyanoacetate | HCID 70693 | — |
| Reactant | 4-Pyridin-2-ylbenzaldehyde | HCID 1515240 | — |
| Solvent | Ethanol | HCID 702 | — |
| Product | HCID 68751051 | HCID 68751051 | 70% |
Reaction Steps
To a solution of 4-(pyridin-2-yl)-benzaldehyde (300 mg, 1.638 mmol) in EtOH (5 ml) at room temperature was added tert-butyl 2-cyanoacetate (0.281 ml, 1.965 mmol) followed by piperidine (0.016 ml, 0.164 mmol). The mixture was stirred at 73° C. overnight. The reaction mixture was cooled to room temperature and concentrated under reduced pressure. To the obtained mixture was added water and then extracted with DCM. The combined organic layer was washed with brine and dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The obtained residue was purified by flash chromatography (silica gel, 15 to 30% EtOAc/Heptane) and gave the title compound: 350 mg (yield: 70%). LCMS (condition B): 307.2 (M+1); retention time=1.30 min.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08877815B2 |
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| Source dataset | uspto-grants-2014_11 |
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| ORD ID | ord-6b95348072a642e38b88d2be4449c864 |
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| Source note | uspto-grants-2014_11 |
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