반응 #58205

반응 방정식

N-[8-azabicyclo[3.2.1]oct-3-yl]acetamide

( 2 )

N-(1-benzylpiperidin-4-yl)-5,7-dimethoxy-4-(4-methoxyphenyl)phthalazin-1-amine

potassium carbonate

2-(bromomethyl)naphthalene

sodium hydroxide

→

pasty oil

수율 84.0%

N-[8-(naphthalen-2-ylmethyl)-8-azabicyclo[3.2.1]oct-3-yl]acetamide

수율 84.0%

용매

acetone

반응 조건

후처리

1. 1
   온도The mixture is refluxed
2. 2
   온도After cooling
3. 3
   기타the acetone is partially evaporated off
4. 4
   workup.ADDITIONWater is added to the residue
5. 5
   추출the mixture is extracted with dichloromethane
6. 6
   추출The organic phase is extracted with 1N hydrochloric acid
7. 7
   기타The acidic aqueous phase obtained
8. 8
   추출extracted with dichloromethane
9. 9
   세척The extract is washed with water and with brine
10. 10
    건조dried over anhydrous sodium sulfate
11. 11
    기타evaporated under reduced pressure
12. 12
    기타The residue obtained
13. 13
    여과is filtered on silica gel (solvent: 95/5 (v/v) dichloromethane/methanol)

실험 절차

1.6 g (9.5 mmol) of N-[8-azabicyclo[3.2.1]oct-3-yl]acetamide prepared according to Dostert et al. (European Journal of Medicinal Chemistry 1984, 19 (2), 105-110) are dissolved in 45 mL of acetone, and 5.2 g of potassium carbonate and 2.5 g (11.4 mmol) of 2-(bromomethyl)naphthalene are added. The mixture is refluxed with stirring for 18 hours. After cooling, the acetone is partially evaporated off. Water is added to the residue, and the mixture is extracted with dichloromethane. The organic phase is extracted with 1N hydrochloric acid. The acidic aqueous phase obtained is basified with 1N sodium hydroxide and then extracted with dichloromethane. The extract is washed with water and with brine, dried over anhydrous sodium sulfate and then evaporated under reduced pressure. The residue obtained is filtered on silica gel (solvent: 95/5 (v/v) dichloromethane/methanol). 2.2 g of a pasty oil are obtained (84% yield).

출처