Benzylamine → HCID 66832926, compound

Temperature

90 °C

(4-Fluorophenyl) divinyl phosphine oxide (1.50 g, 7.65 mmol) and benzylamine (1.05 mL, 9.57 mmol) were dissolved in a mixture of 100 mL of THF and 100 mL of deionized water. The reaction mixture was heated at 90° C. overnight. The reaction mixture was concentrated by rotary evaporation and the product was extracted into dichloromethane and washed with saturated brine. The organic phase was dried with sodium sulfate, filtered, and concentrated by rotary evaporation to yield 2.52 g of crude product. Impurities were removed by passing a solution of the crude product in ethyl acetate through a plug of silica. The product was then eluted from the silica with 10% methanol in ethyl acetate. The solvents were removed by rotary evaporation to yield 1.89 g (6.24 mmol, 82%) of 1-benzyl-4-(4-fluorophenyl)-[1,4]azaphosphinane 4-oxide as a colorless oil. ESMS (m/z): (M+1)+ found, 304.

1. concentrationThe reaction mixture was concentrated by rotary evaporation
2. extractionthe product was extracted into dichloromethane
3. washwashed with saturated brine
4. dry with materialThe organic phase was dried with sodium sulfate
5. filtrationfiltered
6. concentrationconcentrated by rotary evaporation
7. customto yield 2.52 g of crude product
8. customImpurities were removed
9. washThe product was then eluted from the silica with 10% methanol in ethyl acetate
10. customThe solvents were removed by rotary evaporation

ORD record

ord-b42d9bafc50743fab18b44a394cfbfc3

Source dataset

uspto-grants-2011_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08067395B2