Hydrochloric Acid → 4-[4-(1,2-Benzisothiazol-3-yl)-1-piperazinyl]-1-(4-fluorophenyl)-1-butanone hydrochloride

HRID 648200Notes

Reaction equation

HRID 648200 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][C:5]1([C:11]2[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=2)[O:10]CCCO1.[N:18]1([C:24]2[C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=3[S:26][N:25]=2)[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+].Cl>C(#N)C.C(O)C>[ClH:1].[S:26]1[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[C:24]([N:18]2[CH2:19][CH2:20][N:21]([CH2:2][CH2:3][CH2:4][C:5]([C:11]3[CH:12]=[CH:13][C:14]([F:17])=[CH:15][CH:16]=3)=[O:10])[CH2:22][CH2:23]2)=[N:25]1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 27721443-(1-Piperazinyl)-1,2-benzisothiazoleHCID 204569532-(3-Chloropropyl)-2-(4-fluorophenyl)-1,3-dioxane

Product 1

HCID 132324854-[4-(1,2-Benzisothiazol-3-yl)-1-piperazinyl]-1-(4-fluorophenyl)-1-butanone hydrochloride

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6342AcetonitrileSolvent2×

Procedure

Title product hydrochloride. A mixture of 2-(3-chloropropyl)-2-(4-fluorophenyl)-1,3-dioxane (4.31 g., 0.0176 mole), 3-(1-piperazinyl)-1,2-benzisothiazole (3.86 g., 0.0176 mole), powdered potassium carbonate (2.43 g., 0.0176 mole) and potassium iodide (0.88 g., 0.0053 mole) in 180 ml. of dry acetonitrile is refluxed for a 20 hr. period. The reaction mixture is filtered, concentrated in vacuo and residual oil dissolved in chloroform and filtered. Concentration of the filtrate affords an oily residue which is taken up in 100 ml. of ethanol containing 10 ml. of 3 N hydrochloric acid and refluxed for 15 min. period. Acetonitrile is added to the cooled mixture and the solid obtained collected, 3.3 g. m.p. 248°-250° C. Crystallization of this material from ethanol affords analytically pure 4-[4-(1,2-benzisothiazol-3-yl)-1-piperazinyl]-1-(4-fluorophenyl)-1-butanone hydrochloride, m.p. 251°-254° C.

Workup

  1. filtrationThe reaction mixture is filtered
  2. concentrationconcentrated in vacuo and residual oil
  3. dissolutiondissolved in chloroform
  4. filtrationfiltered
  5. customConcentration of the filtrate affords an oily residue which
  6. customthe solid obtained
  7. customcollected
  8. customCrystallization of this material from ethanol

Sources & evidence

ORD record
ord-c2e0f8871274434ba9e94083c1669b26
Source dataset
uspto-grants-1983_10
Patent number
US04411901

Reaction notes

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