Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | tert-Butyl 4-(bromomethyl)piperidine-1-carboxylate | HCID 15512811 | — |
| Reactant | 1,2-Dihydro-3-methyl-1,4,7b-triazacyclopent[cd)inden-2-one | HCID 135810294 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 21190120 | HCID 21190120 | 62.9% |
Reaction Steps
To a suspension of 735 mg (4.24 mmol) of 1,2-dihydro-3-methyl-1,4,7b-triazacyclopent[cd]inden-2-one in 15 ml of DMF was added, while stirring under ice-cooling, 187 mg (4.68 mmol) of 60% sodium hydride (dispersion in oil). The mixture was stirred for 20 minutes at the same temperature. To the mixture was added a solution of 1.18 g (4.24 mmol) of 4-bromomethyl-1-tert-butoxycarbonylpiperidine in 5 ml of DMF. The mixture was stirred for one hour at 100° C. After cooling, the reaction mixture was poured into water and extracted with ethyl acetate. The extract was washed with water and brine, dried over anhydrous magnesium sulfate. The solvent was distilled off, and the residue was purified by column chromatography (eluent: ethyl acetate) to give 988 mg of the desired compound (62.8%, pale yellow 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-b324e46ba23f414e9c5c7c6ba587b8d3 |
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| Source note | uspto-grants-1999_09 |
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