3-(1-Piperazinyl)-1,2-benzisothiazole

3-(1-Piperazinyl)-1,2-benzisothiazole is Yellow Solid

General procedure for synthesis of 3-(piperazin-1-yl)benzo[d]isothiazole 10.2 grams of piperidine, Mix 4.0 g of 3-chloro-1, 2-benzothiazole and 10 ml of ethanol and mix at 80 ° C under refluxAfter 18 hours, it was cooled, poured into water, separated with 100 ml of water and 200 ml of toluene, and the organic phase was washed with 100 ml of water. Dry, filter, concentrate to 20 ml, and refrigerate overnight (0-5 ° C) in the refrigerator. Precipitation appeared, filtered to give a white solid, yield79.6percent.Preparation Example 20: 3-(4-(Benzo[d]isothiazoI-3-yl)piperazin-l- yl)propan-l-amine dihydrochloride; A mixture of piperazine (10.2 g, 0.118 mmol) and 3-chloro-l , 2- benzisothiazole (4.0 g, 0.024 mmol) in t-BuOH (4 mL) was refluxed overnight. The reaction mixture was poured into water (100 mL) and extracted with toluene (200 mL). The organic phase was dried over MgSOPreparation 1 Crude 3-[bis(hydroxyethyl)]amino-l, 2-benzisothiazole (6.0 mmol) was dissolved in 20 ml of acetonitrile and triethylamine (18 mmol). Methanesulfonyl chloride (13 mmol) was dropwise added at 0-4°C. The resulting mixture was stirred at this temperature for 1 hour and at room temperature for 3-5 hours. The reaction mixture was washed with water, dried over sodium sulfate and concentrated. The residue was dissolved in methanol-ammonium hydroxide solution and heated to reflux. After 20-24 hours at reflux, the solution was sampled for thin-layer chromatography (elution with methylene chloride/isopropanol/triethylamine, 15:5: 1) which showed that the reaction was complete. Half volume of methanol was evaporated under reduced pressure and water (30 mL) was added, following by toluene (50 ml). Then the separated aqueous layer was washed with fresh toluene (10 ml). The combined toluene layers were washed with water (20 ml) and then treated with decolorizing carbon. The mixture was heated to reflux and filtered hot through celite. The celite cake was rinsed with toluene (10 mL), and the combined washing and filtrate were concentrated at reduced pressure to 10 mL. Isopropanol (22 ml) was added to the concentrate and the yellowish solution was cooled to 20°C. The pH of the solution was slowly adjusted to 3.5-4.0 with of concentrated hydrochloric acid. The resulting slurry was cooled to 0-5°C, stirred for 1 hour, and then filtered. The product was washed with cold isopropanol and dried in vacuum at 40°C for 24 hours. The title compound (4.32mmol) was isolated as a light yellow solid in 71 percent yield (>98.5percent purity).2.5 g of anhydrous piperazine was dissolved in 5 ml of methylene chloride, and the temperature was controlled at 15 to 20°C. The benzo[d]isothiazole-3-trifluoromethanesulfonate in dichloromethane was added dropwise. The temperature was controlled until the reaction was complete, filtered, washed with water, and the organic layers were separated under reduced pressure to recover the solvent to give 1.86 g of 3-(1-piperazinyl)-1, 2-benzisothiazole compound of formula I.The two-step yield was 85percent and the product purity was 98.9percent. The content of the compound 1, 4-bis(benzo[d]isothiazol-3-yl)piperazine VI in the product was determined by liquid chromatography (HPLC). 0.09percent.

3-(1-Piperazinyl)-1,2-benzisothiazole is a reagent used to synthesize Ziprasidione

Molecular Weight:219.31
XLogP3:2.1
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:1
Exact Mass:219.08301860
Monoisotopic Mass:219.08301860
Topological Polar Surface Area:56.4
Heavy Atom Count:15
Complexity:218
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes