تفاعل #2063066

معادلة التفاعل

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

المردود 34.0%

المذيبات

CHCl3

ظروف التفاعل

المعالجة

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

الإجراء التجريبي

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).

المصدر