1-(4-Methoxyphenyl)-piperazine, dihydrochloride → 3-{2-[4-(4-Methoxyphenyl)-1-piperazinyl]ethyl}-2-trifluoroacetylimino-6-trifluoromethoxybenzothiazoline hydrochloride

HRID 256826

Reaction equation

HRID 256826 reaction equation
[ClH:1].[CH3:2][O:3][C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:15][CH2:14][N:13]([CH2:16][CH2:17]C3C4NC(=NC(=O)C(F)(F)F)SC=4C=C(OC(F)(F)F)C=3)[CH2:12][CH2:11]2)=[CH:6][CH:5]=1.CS(OCC[N:46]1[C:50]2[CH:51]=[CH:52][C:53]([O:55][C:56]([F:59])([F:58])[F:57])=[CH:54][C:49]=2[S:48][C:47]1=[N:60][C:61](=[O:66])[C:62]([F:65])([F:64])[F:63])(=O)=O.Cl.Cl.COC1C=CC(N2CCNCC2)=CC=1>C1(C)C=CC=CC=1>[ClH:1].[CH3:2][O:3][C:4]1[CH:5]=[CH:6][C:7]([N:10]2[CH2:11][CH2:12][N:13]([CH2:16][CH2:17][N:46]3[C:50]4[CH:51]=[CH:52][C:53]([O:55][C:56]([F:59])([F:57])[F:58])=[CH:54][C:49]=4[S:48][C:47]3=[N:60][C:61](=[O:66])[C:62]([F:63])([F:64])[F:65])[CH2:14][CH2:15]2)=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 27237001-(4-Methoxyphenyl)-piperazine, dihydrochlorideHCID 157348642-(2-Trifluoroacetylimino-6-trifluoromethoxy-3-benzothiazolinyl)ethyl methanesulphonateHCID 178491970HCID 178491970, compound

Product 1

HCID 197842683-{2-[4-(4-Methoxyphenyl)-1-piperazinyl]ethyl}-2-trifluoroacetylimino-6-trifluoromethoxybenzothiazoline hydrochloride

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

3-{2-[4-(4-Methoxyphenyl)-1-piperazinyl]ethyl-2-trifluoroacetylimino-6-trifluoromethoxybenzothiazoline hydrochloride may be prepared in the following manner: a mixture of 2-(2-trifluoroacetylimino-6-trifluoromethoxy-3-benzothiazolinyl)ethyl methanesulphonate (4.52 g), toluene (120 cc) and the base liberated from 4-(p-methoxyphenyl)piperazine dihydrochloride (10.56 g) is heated to reflux for 1 hour, cooled to +4° C. and then drained. The toluene filtrate is evaporated under reduced pressure and then treated with 1.2N aqueous hydrochloric acid solution (45 cc). The hydrochloride separates in amorphous form and then crystallizes on grinding with ethanol (50 cc). After draining, washing with ethanol (15 cc) and drying at 50° C. at 20 mmHg, 3-{2-[4-(4-methoxyphenyl)-1-piperazinyl]ethyl}-2-trifluoroacetylimino-6-trifluoromethoxybenzothiazoline hydrochloride (1.7 g) is obtained.

Workup

  1. temperatureis heated
  2. temperatureto reflux for 1 hour
  3. temperaturecooled to +4° C.
  4. customThe toluene filtrate is evaporated under reduced pressure
  5. additiontreated with 1.2N aqueous hydrochloric acid solution (45 cc)
  6. customcrystallizes
  7. customon grinding with ethanol (50 cc)
  8. washwashing with ethanol (15 cc)
  9. customdrying at 50° C. at 20 mmHg

Sources & evidence

ORD record
ord-ee377dbe5f194db99304f6eff0dad590
Source dataset
uspto-grants-1993_11
Patent number
US05260297

Linked notes

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