Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | 2-Chloro-5-(chloromethyl)pyridine | HCID 155479 | — |
| Reactant | 4-Propylpyrrolidin-2-one | HCID 14178100 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Product | HCID 15979680 | HCID 15979680 | 80% |
Reaction Steps
A solution of 4-propylpyrrolidin-2-one x1 (0.50 g, 3.93 mmol, 1 eq) and 2-chloro-5-(chloromethyl)pyridine x37 (0.64 g, 3.93 mmol, 1 eq) in acetonitrile (3 ml) is heated at 50° C. NaH (60% dispersion in oil, 158 mg, 3.93 mmol, 1 eq) and acetonitrile (5 ml) are added and the solution is stirred for 8 h at 50° C. The mixture is then poured on ice/water and the aqueous phase is extracted with CH2Cl2. The combined organic phases are dried over MgSO4, filtered and concentrated to dryness. The crude product is purified by chromatography on silicagel (CH2Cl2/MeOH/NH4OH: 99/1/0.1 (v/v/v)) to afford 790 mg of 1-[(6-chloropyridin-3-yl)methyl]-4-propylpyrrolidin-2-one 228.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08518943B2 |
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| Source dataset | uspto-grants-2013_08 |
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| ORD ID | ord-3703d628ae6048b798f27ba30ed2c964 |
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| Source note | uspto-grants-2013_08 |
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