HuagongsheHuagongshe Chemistry Print Report · For research reference only
Water → 1-[1-(1,2,2a,3,4,5-hexahydroacenaphthylen-1-yl)piperidin-4-yl]-1,3-dihydro-2H-benzimidazol-2-one
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Water | HCID 962 | — |
| Reactant | 1,1'-Carbonyldiimidazole | HCID 68263 | — |
| Reactant | N-[1-(1,2,2a,3,4,5-hexahydroacenaphthylen-1-yl)piperidin-4-yl]-benzene-1,2-diamine | HCID 68704972 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | 1-[1-(1,2,2a,3,4,5-hexahydroacenaphthylen-1-yl)piperidin-4-yl]-1,3-dihydro-2H-benzimidazol-2-one | HCID 59322969 | 61.5% |
Reaction Steps
N-[1-(1,2,2a,3,4,5-Hexahydroacenaphthylen-1-yl)piperidin-4-yl]-benzene-1,2-diamine (1.15 g) was dissolved in THF (70 ml), 1,1′-carbonyldiimidazole (0.591 g) was added, and the mixture was stirred at room temperature for 3 hr. The reaction mixture was poured into water, and the mixture was extracted with ethyl acetate. The extract was washed with water and saturated aqueous ammonium chloride solution, dried over magnesium sulfate, and concentrated. The obtained residue was purified by silica gel column chromatography (chloroform/methanol) to give the title compound (0.76 g) as a white solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08877779B2 |
| Source dataset | uspto-grants-2014_11 |
| ORD ID | ord-7f79c98b39144665b9708f47e354008d |
| Source note | uspto-grants-2014_11 |