Reacción #353987

Ecuación de reacción

1-{1-[4-(3-aminopropoxy)benzoyl]-4-piperidinyl}-3,4-dihydrocarbostyril

benzaldehyde

sodium boron hydride

→

3,4-dihydrocarbostyril

Disolventes

methanol

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturacooled with ice
2. 2
   workup.STIRRINGthe mixture is stirred under ice cooling for 2 hours
3. 3
   workup.WAITto stand at room temperature overnight
4. 4
   workup.DISTILLATIONThe solvent is distilled off
5. 5
   workup.ADDITIONwater is added to the resulting residue
6. 6
   Extracciónthe mixture is extracted with ethyl acetate
7. 7
   LavadoThe extract is washed successively with saturated sodium hydrogen carbonate, water and saline solution
8. 8
   Secadodried with sodium sulfate
9. 9
   workup.DISTILLATIONthe solvent is distilled off
10. 10
    OtroThe resulting residue is purified by silica gel column chromatography (solvent: methanol:dichloromethane=1:100)

Procedimiento

A mixture of 1-{1-[4-(3-aminopropoxy)benzoyl]-4-piperidinyl}-3,4-dihydrocarbostyril (1.4 g), benzaldehyde (0.42 ml) and methanol (15 ml) is stirred at room temperature for 3 hours and cooled with ice. Thereto is added sodium boron hydride (0.21 g) and the mixture is stirred under ice cooling for 2 hours and then allowed to stand at room temperature overnight. The solvent is distilled off and water is added to the resulting residue and the mixture is extracted with ethyl acetate. The extract is washed successively with saturated sodium hydrogen carbonate, water and saline solution, dried with sodium sulfate and then the solvent is distilled off. The resulting residue is purified by silica gel column chromatography (solvent: methanol:dichloromethane=1:100) to give 1-{1-[4-benzylaminopropoxy)benzoyl]-4-piperidinyl}-3,4-dihydrocarbostyril (1.02 g).

Fuente