Reacción #1478582

Ecuación de reacción

hydrogen chloride

nitro

N-(3-{2-[2-(3-aminopropoxy)ethoxy]ethoxy}propyl)-N-(4-nitrophenyl)amine

→

expected product ( 20 )

N-(3-{2-[2-(3-aminopropoxy)ethoxy]ethoxy}propyl)benzene-1,4-diamine Hydrochloride

Disolventes

methanol

methanol

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONwere introduced into a 200 ml autoclave (hydrogenator)
2. 2
   Otroequipped with a magnetic stirrer
3. 3
   OtroThe solution obtained
4. 4
   Otrowas degassed with nitrogen
5. 5
   workup.ADDITION0.4 g of palladium-on-charcoal (5% humidity, comprising 50% water) was added
6. 6
   Otrowhile flushing once with hydrogen, and hydrogen
7. 7
   workup.ADDITIONwas then introduced to a pressure of about 5 bar
8. 8
   OtroAfter reaction for 4 hours
9. 9
   Otrothe reactor was flushed with nitrogen
10. 10
    Filtraciónthe reaction mixture was filtered quickly through Celite under a gentle pressure of nitrogen
11. 11
    LavadoIt was rinsed several times with methanol under a stream of nitrogen
12. 12
    OtroThe solution thus obtained
13. 13
    Concentraciónwas concentrated
14. 14
    workup.ADDITIONwas then treated with ether
15. 15
    OtroThe product obtained, in the form of a pale pink paste
16. 16
    workup.STIRRINGwas stirred
17. 17
    Lavadorinsed several times with acetonitrile and ether under nitrogen

Procedimiento

1.5 g of nitro derivative (19) prepared above and about 100 ml of methanol were introduced into a 200 ml autoclave (hydrogenator) equipped with a magnetic stirrer. The solution obtained was degassed with nitrogen. 0.4 g of palladium-on-charcoal (5% humidity, comprising 50% water) was added thereto. The reaction mixture was stirred, while flushing once with hydrogen, and hydrogen was then introduced to a pressure of about 5 bar. After reaction for 4 hours, the reactor was flushed with nitrogen and the reaction mixture was filtered quickly through Celite under a gentle pressure of nitrogen. The filtrate was recovered in a pre-cooled solution of methanol comprising about 3 equivalents of hydrogen chloride gas. It was rinsed several times with methanol under a stream of nitrogen. The solution thus obtained was concentrated and was then treated with ether. The product obtained, in the form of a pale pink paste, was stirred and then rinsed several times with acetonitrile and ether under nitrogen. 1.6 g of expected product (20) were isolated in the form of a slightly pink white powder.

Fuente