Molbank 2005, M430

http://www.mdpi.net/molbank/

 

N-{(2Z)-4-[4-(3-chlorophenyl)piperazin-1-yl]but-2-enyl}-1,8-naphthalimide

 

Teresa Kowalska, Piotr Kowalski*

 

Institute of Organic Chemistry and Technology, Cracow University of Technology,
24 Warszawska Str., 31-155 Krak車w, Poland.

Phone (+4812)-628-27-22, e-mail: [email protected]

 

Received: 14 July 2004 / Accepted: 15 July 2004 / Published: 1 August 2005

 

Keywords: arylpiperazines, serotonin receptors ligands

 

In continuation of our interest on synthesis and properties of arylpiperazine derivatives investigated as a serotonin receptors ligands [1-3], 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每140 ºC. (for HCl salt mp 279每281 ºC)

 

1H-NMR (80 MHz, CDCl3): 汛= 2.64每2.76 (m, 4H, 2CH2-pip); 3.17每3.30 (m, 4H, 2CH2-pip); 3.39 (d, 2H, CH2-N-pip); 4.87 (d, 2H, CH2-N-imide); 5.68每5.79 (m, 2H, CH=CH); 6.74每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%.

 

References

1. Kowalski, P.; Mokrosz, M. J.; Majka, Z.; Kowalska, T.; Duszy里ska, B. J. Heterocyclic  Chem. 2000, 37, 187-189.

2. Kowalski, P.; Kowalska, T.; Mokrosz, M.J.; Bojarski, A.J.; Charakchieva-Minol, S. Molecules 2001, 6, 784-795.

3. Bojarski, A.J.; Kowalski, P.; Kowalska, T.; Duszy里ska, B.; Charakchieva-Minol, S.; Tatarczy里ska, E.; Kłodzi里ska, A.; Chojnacka-W車jcik, E. Bioorg. Med. Chem. 2002, 10, 3817-3827.

 

Sample Availability: Available from MDPI.

 

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