Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | 2-Piperidone | HCID 12665 | — |
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | HCID 86682946 | HCID 86682946 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Toluene | HCID 1140 | — |
| Product | HCID 86683077 | HCID 86683077 | 64.9% |
Reaction Steps
To a suspension of sodium hydride (31.5 mg, 55% in mineral oil, 0.723 mmol) in toluene (4 ml) was added piperidin-2-one (133 mg, 1.34 mmol) followed by 2,6-dichloro-4-phenyl-quinoline-3-carbonitrile (prepared as described in example 27 step B) (200 mg, 0.669 mmol) and the mixture was heated to 100° C. for 6 h. The reaction mixture was cooled to room temperature, diluted with water and extracted twice with DCM and twice with EtOAc. The combined extracts were washed with brine, dried with Na2SO4 and evaporated. The remaining residue was triturated with cold diethyl ether to afford the title compound (157 mg, 62%) as light yellow solid. MS (ESI): 362.3 (M+H)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09199938B2 |
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| Source dataset | uspto-grants-2015_12 |
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| ORD ID | ord-82847960404149e98e1ec39b6e388063 |
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| Source note | uspto-grants-2015_12 |
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