HuagongsheHuagongshe Chemistry Print Report · For research reference only
Water → 7-(Morpholin-4-yl)-3,4-dihydronaphthalen-1(2H)-one
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Morpholine | HCID 8083 | — |
| Reactant | Potassium Phosphate, Tribasic | HCID 62657 | — |
| Reactant | 7-Bromo-1,2,3,4-tetrahydronaphthalen-1-one | HCID 252731 | — |
| Catalyst | 2-(Di-tert-butylphosphino)biphenyl | HCID 2734215 | — |
| Catalyst | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| Solvent | Toluene | HCID 1140 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | 7-(Morpholin-4-yl)-3,4-dihydronaphthalen-1(2H)-one | HCID 13179502 | 58.4% |
Reaction Steps
A solution of 7-bromo-3,4-dihydro-2H-naphthalen-1-one (600 mg), morpholine (1.16 g), tripotassium phosphate (850 mg), tris(dibenzylideneacetone)dipalladium (0) (24.4 mg) and 2-(di-tert-butylphosphino)biphenyl (15.9 mg) in toluene (5.0 mL) was stirred in a nitrogen atmosphere at 100° C. overnight. Water and ethyl acetate were added to the reaction solution and the organic layer was partitioned. The organic layer was washed with brine, and then dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The resulting residue was purified by silica gel chromatography (elution solvent: heptane-ethyl acetate system) to obtain 360 mg of the title compound. The physical properties of the compound are as follows.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07880009B2 |
| Source dataset | uspto-grants-2011_02 |
| ORD ID | ord-03fa34a7d09148e3a2dd7a949dc36f4e |
| Source note | uspto-grants-2011_02 |