Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Rolipram | HCID 5092 | — |
| Reactant | 1,2-Diaminocyclohexane, trans- | HCID 43806 | — |
| Reactant | Potassium Phosphate, Tribasic | HCID 62657 | — |
| Reactant | 3-Bromothioanisole | HCID 2735627 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | HCID 68828335 | HCID 68828335 | 71% |
Reaction Steps
A mixture of 4-(3-cyclopentyloxy-4-methoxy-phenyl)-pyrrolidin-2-one (276 mg, 1 mmol), 1-bromo-3-methylsulfanylbenzene (1.4 mmol), K3PO4 (1.5 mmol), DMF (3 mL), dioxane (3 mL) and 1,2-trans-cyclohexanediamine (25 μL) was stirred under N2 for 5 min before CuI (35 mg) was added. The reaction mixture was heated at 110° C. for 20 h under N2 with stirring, then cooled down to r.t. The mixture was diluted with EtOAc, washed with saturated NH4Cl (3×10 mL) and dried over Na2SO4. Concentration and chromatography of the residue on silica gel gave 282 mg of pure product. Yield: 71%.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US07601742B2 |
|---|
| Source dataset | uspto-grants-2009_10 |
|---|
| ORD ID | ord-88cc2b29803c4a46919d25d6b129e113 |
|---|
| Source note | uspto-grants-2009_10 |
|---|
