تفاعل #49978

معادلة التفاعل

ammonium acetate

1-benzyl-4-piperidone

pyrrolidine

ethoxymethylenemalononitrile

→

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

المردود 49.5%

المذيبات

toluene

dioxane

ظروف التفاعل

المعالجة

1. 1
   workup.DISTILLATIONwith distilling off water
2. 2
   تركيزThe 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
   درجة الحرارةcooling
6. 6
   workup.STIRRINGthe mixture is stirred at 70° C. overnight
7. 7
   تركيزconcentrated to dryness under reduced pressure
8. 8
   workup.ADDITIONTo the residue is added isopropanol
9. 9
   ترشيحthe precipitate crystals are collected by filtration
10. 10
    غسيلwashed with water
11. 11
    أخرىdried

الإجراء التجريبي

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.

المصدر