반응 #1951063

반응 방정식

divinyl-phosphine oxide

benzylamine

THF

benzylamine

→

1-benzyl-4-(cyclopropylmethyl)-[1,4]azaphosphinane 4-oxide

수율 81.0%

용매

water

반응 조건

후처리

1. 1
   온도the reaction mixture was heated for an additional six hours at 90° C
2. 2
   농축The reaction mixture was concentrated by rotary evaporation
3. 3
   추출the product was extracted into dichloromethane
4. 4
   세척washed with saturated brine
5. 5
   건조The organic phase was dried with sodium sulfate
6. 6
   여과filtered
7. 7
   농축concentrated by rotary evaporation
8. 8
   세척The product was then eluted from the silica with ethanol
9. 9
   기타The solvents were removed by rotary evaporation

실험 절차

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.

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