Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Benzamidine | HCID 2332 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | 2-(5-bromo-4-oxopentyl)-2,3-dihydro-1H-isoindole-1,3-dione | HCID 13903293 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 178514988 | HCID 178514988 | 67.6% |
Reaction Steps
To a solution of 2-(5-bromo-4-oxo-pentyl)-isoindole-1,3-dione [CAS 41306-64-3](12.4 g) in abs. DMF (50 ml) was added benzamidine 85% (5.65 g) and potassium carbonate (11.05 g). The reaction mixture was stirred at 80° C. for 4 h, concentrated under high vacuum, quenched with water and extracted with ethyl acetate. The organic phase was washed with ice/water and brine, dried over magnesium sulphate and concentrated. The residue was purified by chromatography on silica gel using methylene chloride/methanol 2 and 5% as eluent. The product fractions were combined and evaporated to dryness to obtain 2-[3-(2-phenyl-1H-imidazol-4-yl)-propyl]-isoindole-1,3-dione (8.95 g) as a light yellow foam.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07314884B2 |
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| Source dataset | uspto-grants-2008_01 |
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| ORD ID | ord-2c2143e804204ea7acec69877a851e6f |
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| Source note | uspto-grants-2008_01 |
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