HuagongsheHuagongshe Chemistry Print Report · For research reference only
Morpholine → 4-(4-(Tetramethyl-1,3,2-dioxaborolan-2-yl)benzoyl)morpholine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Morpholine | HCID 8083 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 1-Hydroxybenzotriazole | HCID 75771 | — |
| Reactant | 1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride | HCID 2723939 | — |
| Reactant | 4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzoic acid | HCID 2734621 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Solvent | Water ethylacetate | HCID 22728543 | — |
| Product | 4-(4-(Tetramethyl-1,3,2-dioxaborolan-2-yl)benzoyl)morpholine | HCID 2760141 | 81% |
Reaction Steps
To a solution of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoic acid (200 mg, 0.806 mmol) in CH2Cl2 (10 mL) was subsequently added EDCl (232 mg, 1.21 mmol), HOBt (163 mg, 1.21 mmol), morpholine (0.11 mL, 1.21 mmol), and Et3N (0.22 mL, 1.61 mmol). The mixture was stirred at room temperature overnight, treated with EtOAc/H2O, and extracted with EtOAc. The combined extracts were washed with brine, dried over anhydrous Na2SO4, filtered, and concentrated. The residue was purified by flash chromatography to give the title compound (207 mg, 81% yield). MS (m/z): 318 (M+H)+
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09434726B2 |
| Source dataset | uspto-grants-2016_09 |
| ORD ID | ord-bfb0987f2d5d40db82adaa469c290a0e |
| Source note | uspto-grants-2016_09 |