Benzylamine → HCID 66832840, compound

Temperature

90 °C

Cyclopropylmethyl)-divinyl-phosphine oxide (3.56, 22.8 mmol) and benzylamine (3.0 mL, 27.4 mmol) were dissolved in a mixture of THF (100 mL) and deionized water (100 mL). The reaction mixture was heated at 90° C. for 24 hours. The reaction was not complete and so additional benzylamine (1.0 mL, 9.1 mmol) 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 ethyl acetate and passed through a plug of silica. The product was then eluted from the silica with ethanol. The solvents were removed by rotary evaporation to yield 4.835 g of 1-benzyl-4-(cyclopropylmethyl)-[1,4]azaphosphinane 4-oxide (18.38 mmol, 81%) as an off-white crystalline solid. 1H NMR (400 MHz, DMSO) δ 7.38-7.30 (m, 4H); 7.30-7.24 (m, 1H); 3.59 (s, 2H); 2.81-2.63 (m, 4H); 1.94-1.83 (m, 2H); 1.82-1.71 (m, 2H); 1.74-1.68 (d of d, 2H); 0.96-0.83 (m, 1H); 0.56-0.49 (m, 2H); 0.22-0.14 (m, 2H); ESMS (m/z): (M+1)+ found, 264; (M+23)+ found, 286.

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 ethanol
9. customThe solvents were removed by rotary evaporation

ORD record

ord-71c7326f5efa450684d1d7fd7a277511

Source dataset

uspto-grants-2009_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07625880B2