Reaktion #2063066

Reaktionsgleichung

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

Ausbeute 34.0%

Lösungsmittel

CHCl3

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeprepared
2. 2
   Temperaturcooled to 0° C. on an ice-bath
3. 3
   Sonstigethe resulting reaction mixture
4. 4
   Temperaturto slowly warm to room temperature
5. 5
   workup.STIRRINGThe reaction mixture was stirred for 3 hours at 60° C
6. 6
   TemperaturThe mixture was cooled to room temperature
7. 7
   Filtrationthe resulting precipitate was filtered off
8. 8
   workup.STIRRINGstirred
9. 9
   Filtrationfiltered off
10. 10
    Sonstigedried
11. 11
    workup.ADDITIONThis fraction was converted into the free base by addition of aqueous ammonia
12. 12
    ExtraktionThe mixture was extracted with CH2Cl2
13. 13
    SonstigeThe separated organic layer was dried
14. 14
    Filtrationfiltered
15. 15
    Sonstigethe solvent evaporated
16. 16
    SonstigeThe residue was crystallized from CH3CN
17. 17
    Filtrationfiltered off
18. 18
    workup.DISSOLUTIONdissolved in 2-propanone
19. 19
    FiltrationThe precipitate was filtered off
20. 20
    Sonstigedried

Vorschrift

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).

Quelle