Реакция #49975

Уравнение реакции

ammonium acetate

1-benzyl-4-piperidone

pyrrolidine

ethoxymethylenemalononitrile

→

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

Выход 49.5%

Растворители

toluene

dioxane

Условия реакции

Обработка

1. 1
   workup.DISTILLATIONwith distilling off water
2. 2
   КонцентрированиеThe 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
   Температураcooling
6. 6
   workup.STIRRINGthe mixture is stirred at 70° C. overnight
7. 7
   Концентрированиеconcentrated to dryness under reduced pressure
8. 8
   workup.ADDITIONTo the residue is added isopropanol
9. 9
   Фильтрацияthe precipitate crystals are collected by filtration
10. 10
    Промывкаwashed with water
11. 11
    Другоеdried

Методика

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.

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