Benzylamine → HCID 66832490, compound

Temperature

82 °C

Divinyl-(4-Fluorophenylmethyl)-phosphine oxide (0.719 g, 3.42 mmol) and benzylamine (0.45 mL, 4.11 mmol) were dissolved in a mixture of THF (15 mL) and deionized water (15 mL). The reaction mixture was heated at 82° C. for 22 hours. The reaction was not complete and so an additional 0.04 mL of benzylamine was added and the reaction mixture was heated for an additional six hours at 90° C. 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. The crude product was taken up in 1:1 ethyl acetate:dichloromethane and passed through a plug of silica. The product was then eluted from the silica with a solution of 10% methanol in ethyl acetate. The solvents were removed by rotary evaporation to yield 0.84 g of 1-benzyl-4-(4-fluorophenylmethyl)-[1,4]azaphosphinane 4-oxide (2.65 mmol, 77%). 1H NMR (400 MHz, CDCl3) δ 7.34-7.25 (m, 5H); 7.25-7.20 (m, 2H); 7.04-6.98. (m, 2H); 3.6 (s, 2H); 3.17-3.12 (d, 2H); 3.00-2.85 (m, 2H); 2.81-2.66 (m, 2H); 1.98-1.75 (m, 4H).

1. temperaturethe reaction mixture was heated for an additional six hours at 90° C
2. concentrationThe reaction mixture was concentrated by rotary evaporation
3. extractionthe product was extracted into dichloromethane
4. washwashed with saturated brine
5. dry with materialThe organic phase was dried with sodium sulfate
6. filtrationfiltered
7. concentrationconcentrated by rotary evaporation
8. washThe product was then eluted from the silica with a solution of 10% methanol in ethyl acetate
9. customThe solvents were removed by rotary evaporation

ORD record

ord-808e126831ce40d69c81f7e78c43ff81

Source dataset

uspto-grants-2009_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07625880B2