Iodoethane → HCID 9834404, compound

Temperature

100 °C

A mixture of 8-methoxy-2,3,4,5-tetrahydro-1H-1-benzazepine-2-one (2.6 g, 13.6 mmol), NaH (648 mg, 27 mmol) and iodoethane (3 ml, 37 mmol) in anhydrous DMF (50 ml) was vigorously stirred and heated at 100° C. for one hour. The reaction mixture was evaporated under reduced pressure to dryness and the residue dissolved in 100 ml ice-cold water. The resulting brown emulsion was extracted three times with chloroform, the combined extracts were washed with 2% solution of HCl and brine. The organic phase was treated with decolorizing carbon, stirred at room temperature for an hour and filtered through Celite. After drying over anhydrous magnesium sulfate the filtrate was evaporated to dryness. The residual oil was purified by gravity column chromatography on silica gel using 30% THF in n-hexane as an eluent to yield 2.2 g (74%) of the desired compound as a pale yellow oil.

1. customThe reaction mixture was evaporated under reduced pressure to dryness
2. dissolutionthe residue dissolved in 100 ml ice-cold water
3. extractionThe resulting brown emulsion was extracted three times with chloroform
4. washthe combined extracts were washed with 2% solution of HCl and brine
5. additionThe organic phase was treated with decolorizing carbon
6. stirringstirred at room temperature for an hour
7. filtrationfiltered through Celite
8. dry with materialAfter drying over anhydrous magnesium sulfate the filtrate
9. customwas evaporated to dryness
10. customThe residual oil was purified by gravity column chromatography on silica gel using 30% THF in n-hexane as an eluent

ORD record

ord-baaeeeeb10664c618388e6e1a8e0aff0

Source dataset

uspto-grants-2003_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06514965B1