반응 #833551

반응 방정식

Na2CO3

4,6-Dimethyl-2-(2-oxo-ethylsulfanyl)nicotinonitrile

4-(2,3-dihydrobenzo[1,4]dioxin-5-yl)piperazine

sodium triacetoxyborohydride

→

2-{2-[4-(2,3-Dihydrobenzo[1,4]dioxin-5-yl)piperazin-1-yl]ethylsulfanyl}-6-methylnicotinonitrile

용매

1,2-dichloroethane

DMF

반응 조건

후처리

1. 1
   workup.ADDITIONadded until pH
2. 2
   추출The mixture was extracted with ethyl acetate
3. 3
   기타the combined organic phases dried
4. 4
   기타evaporated
5. 5
   기타to give an oil which
6. 6
   기타was subjected to purification by column chromatography (silica gel; ethyl acetate and heptane)
7. 7
   기타giving an oil which
8. 8
   기타precipitated as the oxalate salt (0.36 g) from acetone
9. 9
   기타LC/MS (m/z) 397 (MH+), RT=1.91, purity: 97%

실험 절차

4,6-Dimethyl-2-(2-oxo-ethylsulfanyl)nicotinonitrile (2.9 g) was dissolved in 1,2-dichloroethane (150 mL), a solution of 4-(2,3-dihydrobenzo[1,4]dioxin-5-yl)piperazine (2.6 g) in DMF (150 mL) was added, followed by addition of sodium triacetoxyborohydride (14.9 g) and stirring for 2 h. The mixture was poured on water and Na2CO3 added until pH reached 7-8. The mixture was extracted with ethyl acetate, the combined organic phases dried and evaporated to give an oil which was subjected to purification by column chromatography (silica gel; ethyl acetate and heptane) giving an oil which precipitated as the oxalate salt (0.36 g) from acetone. LC/MS (m/z) 397 (MH+), RT=1.91, purity: 97%.

출처