ChemicalBook CAS DataBase List 3-(1-Piperazinyl)-1,2-benzisothiazole

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

10synthesis methods

Product Name:3-(1-Piperazinyl)-1,2-benzisothiazole
CAS Number:87691-87-0
Molecular formula:C11H13N3S
Molecular Weight:219.31

3-(1-Piperazinyl)-1,2-benzisothiazole is an intermediate for the synthesis of ziprasidone, serotonin (5HT2) and dopamine (D2) receptor antagonists. It can be synthesized by substitution reaction between Piperazine and 3-Chloro-1,2-benzisothiazole.

110-85-0 Synthesis

110-85-0
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7716-66-7 Synthesis

7716-66-7
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87691-87-0
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$10.00/1g

Yield:87691-87-0 85%

Reaction Conditions:

in ethanol at 80; for 36 h;

Steps:

4.1.17. General procedure for synthesis of 3-(piperazin-1-yl)benzo[d]isothiazole
General procedure for synthesis of 3-(piperazin-1-yl)benzo[d]isothiazole
The compound 3-chloro-1, 2-benzisothiazole (1 mmol) was allowed to react with piperazine (1.2 mmol) in Ethanol at 80 °C for 36 h.
Then reaction mixture was concentrate and RM was dissolved in ethyl acetate and washed with water.
Ethylacetate layer dried with Na₂SO₄ and concentrate them and get 3-(piperazin-1-yl)benzo[d]isothiazole.
White solid, 85% yield, mp 215-217 °C, ¹H NMR (400 MHz, CDCl₃): δ = 7.42 (t, J = 7.2 Hz, 1H), 7.29 (m, 3H), 4.14 (t, J = 4.8 Hz, 4H), 3.15 (t, J = 4.8 Hz, 4H); ¹³C NMR (100 MHz, DMSO+CDCl₃): 166.8, 156.2, 135.8, 128.5, 127.6, 125.2, 124.9, 119.8, 53.6, 49.2, 46.6, 45.1, 7.1. MS calcd for C₁₉H₂₀N₄OS₂: 219.31. Found: 220.33, (M⁺); Anal. Calcd for C₁₉H₂₀N₄OS₂: C, 60.24; H, 5.97; N, 19.16; S, 14.62; Found: C, 60.25; H, 5.99; N, 19.13; S, 14.61.

References:

Reddy, Kummetha Indrasena;Srihari, Konduri;Renuka, Janupally;Sree, Komanduri Shruthi;Chuppala, Aruna;Jeankumar, Variam Ullas;Sridevi, Jonnalagadda Padma;Babu, Kondra Sudhakar;Yogeeswari, Perumal;Sriram, Dharmarajan [Bioorganic and Medicinal Chemistry,2014,vol. 22,# 23,p. 6552 - 6563]

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