Reacción #2063066

Ecuación de reacción

4-(3,4-dichlorophenyl)-1-piperazinepropanamine

1-isothiocyanato-4-methoxy-benzene

Thionylchloride

→

N-[3-[4-(3,4-dichlorophenyl)-1-piperazinyl]propyl]-6-methoxy-2-benzothiazolamine dihydrochloride

Rendimiento 34.0%

Disolventes

CHCl3

Condiciones de reacción

Tratamiento posterior

1. 1
   Otroprepared
2. 2
   Temperaturacooled to 0° C. on an ice-bath
3. 3
   Otrothe resulting reaction mixture
4. 4
   Temperaturato slowly warm to room temperature
5. 5
   workup.STIRRINGThe reaction mixture was stirred for 3 hours at 60° C
6. 6
   TemperaturaThe mixture was cooled to room temperature
7. 7
   Filtraciónthe resulting precipitate was filtered off
8. 8
   workup.STIRRINGstirred
9. 9
   Filtraciónfiltered off
10. 10
    Otrodried
11. 11
    workup.ADDITIONThis fraction was converted into the free base by addition of aqueous ammonia
12. 12
    ExtracciónThe mixture was extracted with CH2Cl2
13. 13
    OtroThe separated organic layer was dried
14. 14
    Filtraciónfiltered
15. 15
    Otrothe solvent evaporated
16. 16
    OtroThe residue was crystallized from CH3CN
17. 17
    Filtraciónfiltered off
18. 18
    workup.DISSOLUTIONdissolved in 2-propanone
19. 19
    FiltraciónThe precipitate was filtered off
20. 20
    Otrodried

Procedimiento

A mixture of 4-(3,4-dichlorophenyl)-1-piperazinepropanamine (0.009 mol), prepared according to the procedure described in Example A.5, and 1-isothiocyanato-4-methoxy-benzene (0.009 mol) in CHCl3 (100 ml) was stirred for one hour at room temperature, then cooled to 0° C. on an ice-bath. Thionylchloride (30 ml) was added dropwise and the resulting reaction mixture was allowed to slowly warm to room temperature. The reaction mixture was stirred for 3 hours at 60° C. The mixture was cooled to room temperature and the resulting precipitate was filtered off, stirred in boiling 2-propanone, filtered off, then dried. This fraction was converted into the free base by addition of aqueous ammonia. The mixture was extracted with CH2Cl2. The separated organic layer was dried, filtered and the solvent evaporated. The residue was crystallized from CH3CN, filtered off, dissolved in 2-propanone and converted into the hydrochloric acid salt (1:2) with HCl/2-propanol. The precipitate was filtered off and dried, yielding 1.6 g (34%) of N-[3-[4-(3,4-dichlorophenyl)-1-piperazinyl]propyl]-6-methoxy-2-benzothiazolamine dihydrochloride (comp. 72).

Fuente