Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | N-(5-Bromopentyl)phthalimide | HCID 136770 | — |
| Reactant | HCID 21190144 | HCID 21190144 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 21190257 | HCID 21190257 | 66% |
Reaction Steps
To a suspension of 277 mg (1.60 mmol) of 3,4-dihydro-2-methyl-1,3,7b-triazacyclopent[cd]inden-4-one in 3 ml of DMF was added, while stirring under ice-cooling, 77 mg (1.93 mmol) of 60% sodium hydride (dispersion in oil). The mixture was stirred for 15 minutes at the same temperature. To the reaction mixture was added 521 mg (1.76 mmol) of N-(5-bromopentyl)phthalimide. The mixture was stirred for one hour at 110° C. After cooling, the reaction mixture was poured into water, and extracted with ethyl acetate. The extract solution was washed with an aqueous saline solution, and dried over anhydrous magnesium sulfate. The solvent was distilled off, and the residue was purified by column chromatography (eluent: ethyl acetate/ethanol=10:1) to afford 410 mg of the desired compound (66.0%, a pale brown solid).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US05958942 |
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| Source dataset | uspto-grants-1999_09 |
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| ORD ID | ord-0106c7cef4504fa4ab500e1aac327dc4 |
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| Source note | uspto-grants-1999_09 |
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