HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triethylamine → N-(4-Hydroxy-3-oxo-2,3-dihydro-1H-inden-5-yl)-5-phenylpentanamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Benzenepentanoic acid | HCID 16757 | — |
| Reactant | Diethyl cyanophosphonate | HCID 76257 | — |
| Reactant | 6-Amino-7-hydroxy-2,3-dihydro-1H-inden-1-one hydrobromide | HCID 67353461 | — |
| Solvent | Diethyl Ether | HCID 3283 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | N-(4-Hydroxy-3-oxo-2,3-dihydro-1H-inden-5-yl)-5-phenylpentanamide | HCID 57781279 | 26.3% |
Reaction Steps
6-Amino-7-hydroxyindan-1-one hydrobromide (50 mg, 0.256 mmol) and 5-phenylvaleric acid (54.8 mg, 0.307 mmol) were dissolved in N,N-dimethylformamide (1.3 mL), diethyl cyanophosphate (45.7 μL, 0.307 mmol) and triethylamine (120 μL, 0.896 mmol) were added, and the mixture was stirred at room temperature for 15 min. The reaction solution was diluted with diethyl ether, washed with water and saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate/hexane=10/90→40/60) to give the title compound (21.8 mg, yield 26%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08552037B2 |
| Source dataset | uspto-grants-2013_10 |
| ORD ID | ord-97381974b8e84dc6a5721944638f02d7 |
| Source note | uspto-grants-2013_10 |