Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Benzyl Bromide | HCID 7498 | — |
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | HCID 10187197 | HCID 10187197 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 22671437 | HCID 22671437 | 57% |
Reaction Steps
The 1-[3-(4-diethylcarbamoylphenyl)-3-(3-methoxyphenyl)propyl]-4-(1,3-dihydro-2H-benzimidazol-2-on-1-yl)piperidine (50 mg) obtained in Example 1 was dissolved in N,N-dimethylformamide (1 ml), added with sodium hydride (60% in oil, 7.4 mg) and stirred at room temperature for 1.5 hours. The reaction mixture was added with benzyl bromide (22 μl) and further stirred at 60° C. for 2 hours. The reaction mixture was added with water (5 ml) and extracted twice with ethyl acetate (5 ml). The organic layer was washed with water (10 ml) and dried over anhydrous magnesium sulfate, and then the solvent was evaporated under reduced pressure. The residue was purified by preparative thin layer silica gel column chromatography (developing solvent: ethyl acetate:methanol=10:1) to obtain 33 mg of the title compound. Yield: 57%.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US06790854B2 |
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| Source dataset | uspto-grants-2004_09 |
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| ORD ID | ord-b51dd9fa970142298efb8c0882bca80a |
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| Source note | uspto-grants-2004_09 |
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