HuagongsheHuagongshe Chemistry Print Report · For research reference only
N,N'-Dimethylethylenediamine → 4-(4-Aminophenyl)morpholin-3-one
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | N,N'-Dimethylethylenediamine | HCID 8070 | — |
| Reactant | 4-Iodoaniline | HCID 10893 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | 3-Morpholinone | HCID 66953 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | 4-(4-Aminophenyl)morpholin-3-one | HCID 11194854 | 50.3% |
Reaction Steps
To a blue solution of 3-morpholinone (250 mg, 2.48 mmol), 4-iodoaniline (650 mg, 2.97 mmol), CuI (47 mg, 0.25 mmol) and N,N′-dimethylethylenediamine (0.040 mL, 0.372 mmol) in dioxane (5 mL) in a pressure bottle, K2CO3 (683 mg, 4.95 mmol) was added. The mixture was heated at 110 C overnight. After being cooled to room temperature, the crude dark solution was loaded to two preparative TLC plates, eluted with EtOAc/MeOH (95/5) to give the desired product as off-white solid (240 mg). MS 193.1 (M+H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07678913B2 |
| Source dataset | uspto-grants-2010_03 |
| ORD ID | ord-6a71d6606dd34a08b8129424f10fde45 |
| Source note | uspto-grants-2010_03 |