Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Sodium Iodide | HCID 5238 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | 1-Benzylpiperazine | HCID 75994 | — |
| Reactant | HCID 22117318 | HCID 22117318 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Product | HCID 22117357 | HCID 22117357 | 81% |
Reaction Steps
4-(3-Chloropropylthio)-3-methyl-2-[(2-pyridinylthio)methyl]-pyridine dihydrochloride (0.59 g; 1.5 mmol) is stirred at 100° C. for 24 h in acetonitrile (10 ml) with benzylpiperazine (2.0 mmol) with addition of potassium carbonate (7.5 mmol) and catalytic amounts of sodium iodide. After addition of water, the mixture is extracted with dichloromethane (2×10 ml), the combined organic phases are washed with water, dried and concentrated, and the crude product (yellow oil) is chromatographed on silica gel. The pure product fractions are combined, concentrated, dissolved in ethanol and treated with 3.5 equivalents of conc. hydrochloric acid. The precipitated solid is filtered off, washed with diisopropyl ether and dried. The title compound is obtained as colorless crystals; m.p. 170-172° C.; yield 81% of theory.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US06162809 |
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| Source dataset | uspto-grants-2000_12 |
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| ORD ID | ord-c71a8936287b4758bd6970c7ff26995b |
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| Source note | uspto-grants-2000_12 |
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