1,4-Dioxane → 1-Amino-4-[3-(morpholin-4-yl)phenyl]naphthalene

Temperature

100 °C

The above intermediate (1.49 g, 3.51 mmol) and 1-amino-4-bromonaphthalene (0.69 g, 3.11 mmol) were dissolved in 20 mL anhydrous 1,4-dioxane in a sealable tube under inert gas atmosphere. The solution was degased and purged with nitrogen (2×). Tetrakis(triphenylphosphine)palladium(O) (0.21 g, 0.18 mmol) was added and the solution was degassed and purged with nitrogen again (2×). The tube was sealed and heated to 100° C. for 17 h. After cooling to room temperature the mixture was diluted with EtOAc, saturated aqueous potassium carbonate solution (10 mL) was added and the mixture was stirred for 1 h at room temperature. The mixture was filtered over diatomaceous earth and the layers were separated. The aqueous layer was extracted with EtOAc. The combined organic layers were washed with brine, dried (Na2SO4), filtered and evaporated to dryness. Purification of the residue by flash chromatography afforded 0.363 g (1.19 mmol, 38%) of title compound.

1. customThe solution was degased
2. custompurged with nitrogen (2×)
3. customthe solution was degassed
4. custompurged with nitrogen again (2×)
5. customThe tube was sealed
6. temperatureAfter cooling to room temperature the mixture
7. additionwas diluted with EtOAc, saturated aqueous potassium carbonate solution (10 mL)
8. additionwas added
9. filtrationThe mixture was filtered over diatomaceous earth
10. customthe layers were separated
11. extractionThe aqueous layer was extracted with EtOAc
12. washThe combined organic layers were washed with brine
13. dry with materialdried (Na2SO4)
14. filtrationfiltered
15. customevaporated to dryness
16. customPurification of the residue by flash chromatography

ORD record

ord-54b2d1b0418a48038e25e9b95d769945

Source dataset

uspto-grants-2003_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06608052B2