反応 #49975

反応方程式

ammonium acetate

1-benzyl-4-piperidone

pyrrolidine

ethoxymethylenemalononitrile

→

2-amino-6-benzyl-5,6,7,8-tetrahydro-1,6-naphthyridine-3-carbonitrile

収率 49.5%

溶媒

toluene

dioxane

反応条件

後処理

1. 1
   workup.DISTILLATIONwith distilling off water
2. 2
   濃縮The reaction solution is concentrated to dryness under reduced pressure
3. 3
   workup.ADDITIONto the residue is added anhydrous dioxane (300 ml)
4. 4
   workup.ADDITIONTo the mixture is added dropwise gradually
5. 5
   温度cooling
6. 6
   workup.STIRRINGthe mixture is stirred at 70° C. overnight
7. 7
   濃縮concentrated to dryness under reduced pressure
8. 8
   workup.ADDITIONTo the residue is added isopropanol
9. 9
   ろ過the precipitate crystals are collected by filtration
10. 10
    洗浄washed with water
11. 11
    その他dried

実験手順

A solution of 1-benzyl-4-piperidone (26.8 g, 0.14 mole) and pyrrolidine (20 g, 0.28 mole) in toluene (300 ml) is refluxed for 4 hours with distilling off water. The reaction solution is concentrated to dryness under reduced pressure, and to the residue is added anhydrous dioxane (300 ml). To the mixture is added dropwise gradually with stirring a solution of ethoxymethylenemalononitrile (19 g, 0.16 mole) in anhydrous dioxane (40 ml) under ice-cooling. The mixture is warmed to room temperature, and stirred for one hour. To the mixture is added ammonium acetate (22 g, 0.29 mole), and the mixture is stirred at 70° C. overnight, and concentrated to dryness under reduced pressure. To the residue is added isopropanol, and the precipitate crystals are collected by filtration, washed with water, and dried to give 2-amino-6-benzyl-5,6,7,8-tetrahydro-1,6-naphthyridine-3-carbonitrile (18.3 g, yield; 49%), which is used in the subsequent reaction without purification.

出典