HuagongsheHuagongshe Chemistry Print Report · For research reference only
Acetic Acid → 1-Ethyl-3,3,5-trimethyl-7-[4-(2-oxo-3,4-dihydro-2H-quinolin-1-yl)piperidin-1-ylmethyl]-1,5-dihydrobenzo[b][1,4]diazepine-2,4-dione
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Acetic Acid | HCID 176 | — |
| Reactant | Sodium triacetoxyborohydride | HCID 5049666 | — |
| Reactant | 1-(piperidin-4-yl)-3,4-dihydroquinolin-2(1H)-one | HCID 10728185 | — |
| Reactant | 1-ethyl-3,3,5-trimethyl-2,4-dioxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepine-7-carbaldehyde | HCID 86670476 | — |
| Solvent | 1,2-Dichloroethane | HCID 11 | — |
| Product | 1-Ethyl-3,3,5-trimethyl-7-[4-(2-oxo-3,4-dihydro-2H-quinolin-1-yl)piperidin-1-ylmethyl]-1,5-dihydrobenzo[b][1,4]diazepine-2,4-dione | HCID 70656734 | 56.8% |
Reaction Steps
1-Ethyl-3,3,5-trimethyl-2,4-dioxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepine-7-carbaldehyde(0.203 g) and acetic acid(0.063 ml) were added to a 1,2-dichloroethane solution (5 ml) of 1-(piperidin-4-yl)-3,4-dihydroquinolin-2(1H)-one (0.170 g), and the mixture was stirred at room temperature for 30 minutes. Sodium triacetoxyborohydride(0.235 g) was added, and the mixture was stirred at room temperature overnight. The reaction mixture was condensed under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate: methanol=100:0→90:10). The purified product was condensed to dryness to give the title compound(0.205 g) as pale yellow amorphous.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09212187B2 |
| Source dataset | uspto-grants-2015_12 |
| ORD ID | ord-e30bf56239e14b33a1f4f010dfb86196 |
| Source note | uspto-grants-2015_12 |