N-{(2Z)-4-[4-(3-chlorophenyl)piperazin-1-yl]but-2-enyl}-1,8-naphthalimide
Institute of Organic Chemistry and Technology, Cracow University of Technology, 24 Warszawska Str., 31-155 Kraków, Poland
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Molbank 2005, 2005(3), M430; https://doi.org/10.3390/M430
Submission received: 14 July 2004
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Accepted: 15 July 2004
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Published: 1 August 2005
In continuation of our interest on synthesis and properties of arylpiperazine derivatives investigated as a serotonin receptors ligands [1,2,3], herein we presented one-pot synthesis of N-{(2Z)-4-[4-(3-chlorophenyl)piperazin-1-yl]but-2-enyl}-1,8-naphthalimide (4). Starting materials e.g. 1,8-naphthalimide (1), (Z)-1,4-dichloro-2-butene (2), and 1-(3-chlorophenyl)piperazine hydrochloride (3) were commercially available reagents.
A mixture of the 1,8-naphthalimide (1) (3.94 g, 0.02 mole), powdered K2CO3 (4.14 g, 0.03 mole), catalytic amount of KI, and 40 mL of DMF was stirred at ambient temperature for 2 h. Than the (Z)-1,4-dichloro-2-butene (2) (2.50 g, 0.02 mole) was added and the stirring continued for another 10 h. Next, a new portion of anhydrous K2CO3 (5.25 g, 0.04 mole) and 1-(3-chlorophenyl)piperazine hydrochloride (3) (4.66 g, 0.02 mole) was added and the reaction mixture was stirred again for 10 h. The mixture was filtrated and the filtrate evaporated. The residue was suspended in 50 mL of acetone, which was decanted from semisolids, and the procedure repeated to give solid crystals. This material purified by crystallization with 1-butanol afforded of the desired N-{(2Z)-4-[4-(3-chlorophenyl)piperazin-1-yl]but-2-enyl}-1,8-naphthalimide (4) (3.1 g, 35%) as the light yellow crystals. For biological experiments the base 4 was converted into hydrochloride salt with ethanol saturated with HCl.
Melting point: 138–140 °C. (for HCl salt mp 279–281 °C)
1H-NMR (80 MHz, CDCl3): δ= 2.64–2.76 (m, 4H, 2CH2-pip); 3.17–3.30 (m, 4H, 2CH2-pip); 3.39 (d, 2H, CH2-N-pip); 4.87 (d, 2H, CH2-N-imide); 5.68–5.79 (m, 2H, CH=CH); 6.74–7.26 (m, 4H, ArH); 7.74 (t, 2H, H3,6-imide); 8.22 (d, 2H, H4,5-imide); 8.61(d, 2H, H2,7-imide).
IR (KBr, cm-1): 2954-2780 (CH); 1699, 1663 (C=O); 1590-1435 (C=C).
MS (EI, 70 eV; m/z, rel.%): 445 [M+] (21); 250 (61); 235 (100); 196 (15); 180 (32).
Elemental Analysis: Calculated for C26H24ClN3O2.HCl (482.41): C, 64.73%; H, 5.22%; N, 8.71%. Found: C, 64.79%; H, 5.33%; N, 8.48%.
Supplementary materials
Supplementary File 1Supplementary File 2Supplementary File 3References
- Kowalski, P.; Mokrosz, M. J.; Majka, Z.; Kowalska, T.; Duszyńska, B. J. Heterocyclic Chem. 2000, 37, 187–189.
- Kowalski, P.; Kowalska, T.; Mokrosz, M.J.; Bojarski, A.J.; Charakchieva-Minol, S. Molecules 2001, 6, 784–795.
- Bojarski, A.J.; Kowalski, P.; Kowalska, T.; Duszyńska, B.; Charakchieva-Minol, S.; Tatarczyńska, E.; Kłodzińska, A.; Chojnacka-Wójcik, E. Bioorg. Med. Chem. 2002, 10, 3817–3827. [PubMed]
- Sample Availability: Available from MDPI.
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Kowalska, T.; Kowalski, P. N-{(2Z)-4-[4-(3-chlorophenyl)piperazin-1-yl]but-2-enyl}-1,8-naphthalimide. Molbank 2005, 2005, M430. https://doi.org/10.3390/M430
AMA Style
Kowalska T, Kowalski P. N-{(2Z)-4-[4-(3-chlorophenyl)piperazin-1-yl]but-2-enyl}-1,8-naphthalimide. Molbank. 2005; 2005(3):M430. https://doi.org/10.3390/M430
Chicago/Turabian StyleKowalska, Teresa, and Piotr Kowalski. 2005. "N-{(2Z)-4-[4-(3-chlorophenyl)piperazin-1-yl]but-2-enyl}-1,8-naphthalimide" Molbank 2005, no. 3: M430. https://doi.org/10.3390/M430
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