反応 #2063066

反応方程式

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

収率 34.0%

溶媒

CHCl3

反応条件

後処理

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

実験手順

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).

出典