반응 #2063066

반응 방정식

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

수율 34.0%

용매

CHCl3

반응 조건

후처리

1. 1
   기타prepared
2. 2
   온도cooled to 0° C. on an ice-bath
3. 3
   기타the resulting reaction mixture
4. 4
   온도to slowly warm to room temperature
5. 5
   workup.STIRRINGThe reaction mixture was stirred for 3 hours at 60° C
6. 6
   온도The mixture was cooled to room temperature
7. 7
   여과the resulting precipitate was filtered off
8. 8
   workup.STIRRINGstirred
9. 9
   여과filtered off
10. 10
    기타dried
11. 11
    workup.ADDITIONThis fraction was converted into the free base by addition of aqueous ammonia
12. 12
    추출The mixture was extracted with CH2Cl2
13. 13
    기타The separated organic layer was dried
14. 14
    여과filtered
15. 15
    기타the solvent evaporated
16. 16
    기타The residue was crystallized from CH3CN
17. 17
    여과filtered off
18. 18
    workup.DISSOLUTIONdissolved in 2-propanone
19. 19
    여과The precipitate was filtered off
20. 20
    기타dried

실험 절차

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).

출처