New benzylpiperazine derivatives bearing mono- And bis-dialkyl substituted 1,2,4-triazoles

Article abstract of DOI:10.1002/hc.20061

Cycloaddition of the 1-aza-2-azonia-allenes 3 with p-cyanobenzyl chlorides afforded, after spontaneous rearrangement, the 1,5-dialkyl-3-[4-chloromethyl) phenyl]-1H-[1,2,4]-triazoles 6. A series of 1,5-dialkyl-1H-[1,2,4]-triazol-3-yl) benzyl-piperazines 7

Full text of DOI:10.1002/hc.20061

Heteroatom Chemistry
Volume 16, Number 1, 2005
New Benzylpiperazine Derivatives Bearing
Mono- and Bis-dialkyl Substituted
1,2,4-Triazoles
Yaseen A. Al-Soud,1 Mohammed N. A. Qalalweh,1
Haitham H. Al-Sa’doni,1 and Najim A. Al-Masoudi2
1Department of Chemistry, College of Science, University of Al al-Bayt, Al-Mafraq, Jordan
2Formerly Fachbereich Chemie, Universita¨t Konstanz, Postfach 5560, D-78457 Konstanz, Germany
Received 23 August 2004; revised 22 September 2004
agent clozapine [14], tryptase inhibitors [15,16],
ABSTRACT: Cycloaddition of the 1-aza-2-azonia-
antiplatelet agents with antivasodialatory effect
allenes 3 with p-cyanobenzyl chlorides afforded,
[17], sedative and tranquilizers [18], antihelminitic
after spontaneous rearrangement, the 1,5-dialkyl-
and antifilarial agents [19], antineoplastic agents
3-[4-chloromethyl)phenyl]-1H-[1,2,4]-triazoles 6. A
[7,20,21], as well as antagonist of postsynaptic recep-
series of 1,5-dialkyl-1H-[1,2,4]-triazol-3-yl)benzyl-
tors 5-HT1A [22,23]. The pharmacological potency
piperazines 7 and 8 were prepared from direct conden-
of such substituted piperazines, as well as the bi-
sation of 6 with piperazine and N-methylpiperazine,
ological activity of 1,2,4-triazole analogues such as
respectively. The structures of the newly synthesized
fluconazole [24] prompted us to prepare a new series
products were identified by 2D NMR spectroscopy.
of 1,4-disubtituted piperazines carrying substituted
ꢀ
C
2005 Wiley Periodicals, Inc. Heteroatom Chem
1,2,4-triazoles and/or methyl group, as potential
antitumor candidates.
16:28–32, 2005; Published online in Wiley InterScience
(www.interscience.wiley.com). DOI 10.1002/hc.20061
RESULTS AND DISCUSSION
INTRODUCTION
Recently, the 4,5-dihydro-3H-pyrazolium salts have
Several heterocycles containing piperazines residues
have been described as potent chemotherapeutic
agents. Recently, some compounds bearing piper-
azines residue were described as highly specific in-
hibitory of HIV-1 replication, such as bis-(indolyl)-
piperazine (BHAP) [4] and trovirdine derivative
[5]. Other various 1,2-dialkyl piperazines have been
reported as antibacterial [6–8], antiprotozoacidal
[9], antihypertensive [10,11], coronary dilators [12],
H-3 antagonists [13], such as the antipsychotic
been synthesized from the cycloaddition of the
short-lived 1-(chloroalkyl)-1-aza-2-azoniaallene hex-
achloroantimonates 3 [25–27] to various electron-
rich alkenes in the presence of Lewis acids like SbCl5;
similarly numerous compounds of 1,2,4-triazoles
were prepared recently in our laboratory via the
cycloaddition of the nitrile derivatives to intermedi-
ates 3. Such examples of our recent work are 1,2,4-
triazole C-nucleosides [28,29], acyclic C-nucleosides
[30], pyrimidines [31], N-alkylphthalimides [32], D-
manno-pentitol-1-yl-1,2,4-triazoles [33], 1H-indoles
as well as quinolines [34], benzotriazoles [35], 3ꢁ-tri-
azolothymidines [36], N,Nꢁ-trisubstituted 1,2,4-tri-
azolo-piperazines [37], and 1,2,4-triazole derivatives
Correspondence to: Najim A. Al-Masoudi; e-mail: Najim.Al-
Masoudi@gmx.de.
c
ꢀ
2005 Wiley Periodicals, Inc.
28

New Benzylpiperazine Derivatives Bearing Mono- and Bis-dialkyl Substituted 1,2,4-Triazoles 29
of acetic acid alkylidene hydrazides [38]. In the
Next, condensation of 6a–d with piperazine in
the ratio of (2:1) in the presence of NaH or K2CO3 and
DMF at 25◦C for 48 h afforded, after recrystallization
from the appropriate solvent, the desired products
of 1,4-bis-(1,5-dialkyl-1H-[1,2,4]-triazol-3-ylbenzyl)-
piperazines 7a–d in 85–87% yield (Scheme 1). These
compounds were identified by homo- and heteronu-
clear NMR spectroscopic methods, HMBC [41], and
present study, we prepared the 3-[4-(chloromethyl)-
phenyl]-1,5-dimethyl-1H-1,2,4-triazole 6a and 6c,
according to our reported method during the prepa-
ration of 6b and 6d [34], from the cycloaddition
of 3 to 4-cyanobenzyl chloride 1. Thus, the dichlo-
rides 2 were converted, at approximately −60◦C,
to the salts 3 in the presence of SbCl5. At −30◦C,
the color changed indicating that 3 underwent cy-
cloaddition with the nitrile 1 to give the insepara-
ble 5-[4-chloromethyl)-phenyl]-3H-1,2,4-triazolium
hexachloroantimonates 4. As the temperature was
raised above −30◦C, 4 rearranged to protonated tri-
azole 5 by [1,2] migration [39,40] of the alkyl group
(R2) at C-3 to N-2, accompanied by elimination of the
CClR1R2 group. In situ hydrolysis of 5 with aqueous
NaHCO3 and aqueous NH3 afforded the triazoles 6a
and 6c in 65 and 73% yield, respectively.
1
mass spectra. The H NMR spectra of 7a–d showed
similar patterns. The CH2-1ꢁ appeared as singlets at δ
3.53, 3.61, 3.54, and 3.55, respectively. The two dou-
blets at δ 7.97, 7.42 (8.2 Hz); 7.99, 7.38 (8.1 Hz); 8.00,
7.37 (7.7 Hz), and 7.97, 7.35 (8.2 Hz), respectively,
were attributed for the symmetrical four aromatic
protons. The alkyl groups at N-1ꢁꢁ and C-5ꢁꢁ were as-
signed. The 13C NMR spectra of 7a–d contained the
resonance signals of the triazole carbons ring (C-3ꢁꢁ,
C-5ꢁꢁ of 7a,b) and (C-2ꢁꢁ, C-10ꢁꢁ of 7c,d) at higher fields
SCHEME 1 Reagents and conditions: i. 2, SbCl5, CH2Cl2, −60◦C; ii. CH2Cl2, −60◦C to 23◦C; iii. NaHCO3, NH3, MeCN,
0◦C, 2h; iv. piperazine, NaH or K2CO3; v. methylpiperazine K2CO3, DMF.

30 Al-Soud et al.
between δ 159.5–161.5 and δ 151.8–157.8, respec-
tively. Due to the identical groups attached at N-1
and N-4, the carbon atoms of piperazine ring of 7a–
d appeared as broad singlets at δ 53.1, 53.1, 51.4, and
51.1, respectively. Compound 7d was selected for this
NMR study showing a 3 JC,H between C-10ꢁꢁ at δ 157.8
Hz, Ar); 4.18 (t, 2H, J = 6.0 Hz, CH2-5ꢁꢁ); 4.27 (s,
2H, CH2-1ꢁ); 3.28 (t, 2H, J = 6.1 Hz, CH2-6ꢁꢁ); 2.20
(m, 2H, CH2-7ꢁꢁ); 2.07 (m, 2H, CH2-8ꢁꢁ). 13C-NMR
(CDCl3): 153.9 (C-2ꢁꢁ); 152.1 (C-10ꢁꢁ); 140.8, (Ar-C);
129.1 (Ar-2 × C); 128.7 (Ar-C); 127.3 (Ar-2 × C);
47.99 (C-5ꢁꢁ); 45.3. (C-1ꢁ); 21.9 (C-7ꢁꢁ); 21.7 (C-6ꢁꢁ);
18.3 (C-8ꢁꢁ). Anal. calc. for C13H14ClN3 (247.72): C,
63.03; H, 5.70; N, 16.96. Found: C, 62.82; H, 5.61; N,
16.67; MS: m/z (%) (EI) 246/248 (85).
2
and CH2-5ꢁꢁ at δ 4.18, as well as a JC,H between Ar-
quart. C at 138.7 and CH2-1ꢁ at δ 3.53. An obvious
3 JC,H correlation was shown between C-5ꢁꢁ at δ 53.0
and CH2-7ꢁꢁ at δ 1.77, as well. The antitumor activity
is under investigation.
Similarly, the 1-(1,5-dialkyl-1H-[1,2,4]-triazol-3-
ylbenzyl)-4-methylpiperazines 8a–d were prepared
from condensation of 6 with N-Me-piperazine in
DMF as a solvent and K2CO3 for 48 h at 25◦C in 28,
33, 40, 29% yields, respectively (Scheme 1).
Preparation of 1,4-bis-[(1,5-dialkyl-1H-[1,2,4]-
triazol-3-yl)benzyl]-piperazines (7)
To a solution of piperazine (0.086 g, 1.00 mmol) in
DMF (7 mL) was stirred K2CO3 (0.22 g, 2.10 mmol)
and stirred for 3 min at 25◦C, followed by addition
of 6 (2.10 mmol). After stirring at 25◦C for 48 h, the
solvent was evaporated to dryness and the residue
was partitioned between CH2Cl2 (40 mL) and water
(20 mL) and the organic layer was dried (Na2SO4),
filtered, and evaporated to dryness. The residue was
stirred with petroleum ether and filtered, dried to
give 7 as a pure solid.
EXPERIMENTAL [28–37]
Preparation of 1,5-dialkyl-3-[4-chloromethyl)-
phenyl]-1H-[1,2,4]-triazoles (6)
To a stirred, cooled (−60◦C) solution of 2 (5.0 mmol)
and 1 (0.76 g, 5.0 mmol) in dry CH2Cl2 (20 mL) was
added dropwise a solution of SbCl5 (4.20 g, 5.0 mmol)
in dry CH2Cl2 (20 mL). The solution was left with
stirring at −60◦C for 1 h, then at 0◦C for 1 h, and fi-
nally at 23◦C for 10 min, followed by addition of pen-
tane (50 mL). The precipitated solid was dissolved in
CH3CN (40 mL), cooled to 0◦C followed by addition
of an aqueous solution of NaHCO3 (2.55 g, 30 mmol
in 30 mL of water) and NH3 solution (2 mL). The mix-
ture was stirred at room temperature for 2 h, then the
organic solvent was evaporated and the residue was
extracted with CHCl3 (3 × 20 mL). The combined
organic extracts were dried (Na2SO4), filtered, and
evaporated to dryness and the residue was recrystal-
lized from petroleum ether.
1,4-Bis-[(1,5-dimethyl-1H-[1,2,4]-triazol-3-yl)-
benzyl]-piperazine (7a). From 6a (0.46 g). Yield:
0.82 g (85%); mp 250–255◦C, decomp. at 267◦C.
1H-NMR (CDCl3): δ 7.97 (d, 2H, J 8.2 Hz, Ar); 7.42
(s, 2H, J 8.2 Hz, Ar); 3.84 (s, 3H, N-Me); 3.53 (s,
2H, CH2-1ꢁ); 2.49 [br s, 11H, 4 × (CH2) of piperazine;
C5-Me]. 13C-NMR (CDCl3): δ 161.5 (C-3ꢁꢁ); 152.7
(C-5ꢁꢁ); 139.1, 129.9 (Ar-2 × C), 129.3 (Ar-2 × C);
127.3 (Ar-C); 125.9 (Ar-C); 62.8 (C-1ꢁ); 53.1 (4 ×
C-piperazine); 35.1 (N-CH3); 11.8 (C5-CH3). Anal.
calc. for C26H32N8 (456.59): C, 68.39; H, 7.06; N,
24.54. Found: C, 67.91; H, 6.89; N, 24.48; MS: m/z
(%) (EI) 456 (90).
1,4-Bis-(1-ethyl-5-methyl-1H-[1,2,4]-triazol-3-yl)-
benzyl]-piperazine (7b). From 6b (0.49 g). Yield:
0.86 g (85%); mp 200–205◦C. 1H-NMR (CDCl3): δ
7.99 (d, 2H, J = 8.1 Hz, Ar); 7.38 (d, 2H, J 8.1 Hz,
Ar); 4.14 (q, 2H, J = 7.0 Hz, CH2CH3); 3.81 (s, 3H,
N-Me); 3.61 (s, 2H, CH2-1ꢁ); 2.59 [br s, 8H, 4 ×
(CH2) of piperazine]; 1.48 (t, 3H, CH2CH3). 13C-NMR
(CDCl3): δ 160.6 (C-3ꢁꢁ); 151.8 (C-5ꢁꢁ); 139.0, 130.1,
129.3 (4 × C); 127.8, 125.9 (2 × C); 62.8 (C-1ꢁ); 53.1
(4 × C-piperazine); 43.3 (CH2CH3); 14.1 (CH2CH3);
11.8 (C5-Me). Anal. calc. for C28H36N8 (484.64): C,
69.39; H, 7.49; N, 23.12. Found: C, 69.02; H, 7.34; N,
22.95; MS: m/z (%) (EI) 484 (80).
3-[4-(Chloromethyl)phenyl]-1,5-dimethyl-1H-
1,2,4-triazole (6a). From 2a (0.92 g). Yield: 0.72 g
1
(65%); mp 150–155◦C. H-NMR (CDCl3): δ 8.03 (d,
2H, J = 8.5 Hz, Ar); 7.43 (s, 2H, J = 8.4 Hz, Ar);
4.60 (s, 2H, CH2-1ꢁ); 3.83 (s, 3H, N-Me); 2.49 (s,
3H, C5-Me). 13C-NMR (CDCl3): δ 159.7 (C-3ꢁꢁ); 152.9
(C-5ꢁꢁ); 139.6, 128 (Ar-2 × C), 129.3 (Ar-2 × C); 127.8
(Ar-C); 126.4 (Ar-C); 45.9 (C-1ꢁ); 35.2 (N-CH3); 11.7
(C5-CH3). Anal. calc. for C11H12ClN3 (221.69): C,
59.60; H, 5.46; N, 18.95. Found: C, 59.31; H, 5.32; N,
18.73; MS: m/z (%) (EI) 220/222 (80).
2-[4-(Chloromethyl)phenyl)]-5,6,7,8-tetrahydro-
[1,2,4]-triazolo[1,5-a]pyridine (6c). From 2c (1.18 g).
Yield: 0.90 g (73%); mp 110–115◦C. 1H-NMR (CDCl3):
δ 8.12 (d, 2H, J = 8.0 Hz, Ar); 7.47 (s, 2H, J = 8.0
1,4-Bis-[(5,6,7,8-tetrahydro-1H-[1,2,4]triazolo-
[1,5-a]pyridin-2-yl)benzyl]-piperazine (7c). From 6c
(0.52 g). Yield: 0.90 g (85%); mp 270–275◦C, decomp.

New Benzylpiperazine Derivatives Bearing Mono- and Bis-dialkyl Substituted 1,2,4-Triazoles 31
at 315◦C. 1H-NMR (CDCl3): δ 8.00 (d, 2H, J = 7.7 Hz,
(285.4): C, 67.34; H, 8.12; N, 24.54. Found: C, 66.96;
H, 8.04; N, 24.28; MS: m/z (%) (EI) 285 (50).
Ar); 7.37 (d, 2H, J = 7.7 Hz, Ar); 4.18 (t, 2H, J = 6.0
Hz, CH2-5ꢁꢁ); 3.54 (s, 2H, CH2-1ꢁ); 2.97 (t, 2H, J = 6.0
Hz, CH2-6ꢁꢁ); 2.51 [br s, 8H, 4 × (CH2) of piperazine];
2.09 (m, 2H, CH2-7ꢁꢁ); 2.00 (m, 2H, CH2-8ꢁꢁ). 13C-NMR
(CDCl3): δ 159.5 (C-2ꢁꢁ); 151.5 (C-10ꢁꢁ); 137.4, 130.0
(Ar-2 × C); 127.7, 127.6 (Ar-2 × C); 124.4 (Ar-2 ×
C); 61.2 (C-1ꢁ); 51.4 (4 × C-piperazine); 45.4 (C-5ꢁꢁ);
22.1 (C-7ꢁꢁ); 21.3 (C-6ꢁꢁ); 18.9 (C-8ꢁꢁ). Anal. calc.
for C30H36N8 (508.67): C, 70.84; H, 7.13; N, 22.03.
Found: C, 70.62; H, 6.97; N, 21.74; MS: m/z (%) (EI)
508 (50).
1-[(1-Ethyl-5-methyl-1H-[1,2,4]-triazol-3-yl)-
benzyl]-4-methylpiperazine (8b). From 6b (0.46 g).
1
Yield: 0.20 (33%); mp 78–80◦C. H-NMR (CDCl3): δ
7.93 (d, 2H, J = 8.1 Hz, Ar); 7.30 (s, 2H, J = 8.1 Hz,
Ar); 4.10 (q, 2H, J = 7.1 Hz, N-CH2CH3); 3.45 (s,
2H, CH2-1ꢁ); 2.48 [br s, 8H, 4 × (CH2) of piperazine];
ꢁ
2.42 (s, 3H, N-Me-piperazine), 2.29 (s, 3H, C5 -Me);
1.40 (t, 3H, N-CH2CH3). 13C-NMR (CDCl3): δ 160.5
(C-3ꢁ); 151.9 (C-5ꢁ); 138.7, 130.2 (Ar-2 × C), 129.3
(Ar-2 × C); 126.0 (Ar-C); 125.9 (Ar-C); 62.7 (C-1ꢁ);
54.9, 52.6 (4 × C-piperazine); 44.2 (N-Me-piperazine);
1,4-Bis-[(6,7,8,9-tetrahydro-5H-[1,2,4]triazolo-
[1,5-a]azepin-2-yl)benzyl]-piperazine (7d). From 6d
(0.55 g). Yield: 0.98 g (87%); mp 280–285◦C. 1H-NMR
(CDCl3): δ 7.97 (d, 2H, J = 8.2 Hz, Ar); 7.35 (d, 2H,
J = 8.2 Hz, Ar); 4.29 (t, 2H, J = 5.2 Hz, CH2-5ꢁꢁ);
3.53 (s, 2H, CH2-1ꢁ); 2.97 (t, 2H, J = 6.4 Hz, CH2-6ꢁꢁ);
2.49 [br s, 8H, 4 × (CH2) of piperazine]; 1.87 (t,
2H, J = 7.5 Hz, CH2-8ꢁꢁ); 1.80 (m, 2H, CH2-9ꢁꢁ); 1.77
(t, 2H, J = 5.2 Hz, CH2-7ꢁꢁ). 13C-NMR (CDCl3): δ
159.5 (C-2ꢁꢁ); 157.8 (C-10ꢁꢁ); 138.7, 129.3 (Ar-2 × C);
129.1 (Ar-C); 127.3 (Ar-C); 125.8 (Ar-2 × C); 62.8
(C-1ꢁ); 53.0 (C-5ꢁꢁ); 51.1 (C-piperazine); 30.3 (C-7ꢁꢁ);
27.5 (C-6ꢁꢁ); 27.4 (C-9ꢁꢁ); 25.0 (C-8ꢁꢁ). Anal. calc. for
C32H40N8 (536.7): C, 71.61; H, 7.51; N, 20.88. Found:
C, 71.40; H, 7.39; N, 19.54; MS: m/z (%) (EI) 536
(45).
ꢁ
43.4 (C5-CH2CH3); 15.2 (C5-CH2CH3); 11.9 (C5 -CH3).
Anal. calc. for C17H25N5 (299.4): C, 68.19; H, 8.42; N,
23.39. Found: C, 67.87; H, 8.31; N, 23.10; MS: m/z
(%) (EI) 299 (95).
1-[(5,6,7,8-Tetrahydro-1H-[1,2,4]triazolo[1,5-a]-
pyridin-2-yl)benzyl]-4-methylpiperazine (8c). To a
suspension of methylpiperazine (0.20 g, 2.00 mmol)
in EtOH (10 mL) was added Na2CO3 (0.21 g,
2.00 mmol), followed by addition of 6c (0.50 g,
2.00 mol). After stirring at 25◦C for 48 h, the solvent
was evaporated to dryness, and the residue was
worked-up as in ‘method a’ to give 8c (0.25 g, 40%),
1
as a yellow solid; mp 250–254◦C. H-NMR (CDCl3):
δ 7.99 (d, 2H, J = 8.0 Hz, Ar); 7.37 (d, 2H, J = 8.0
Hz, Ar); 4.18 (br s, 2H, CH2-9ꢁꢁ); 3.53 (s, 2H, CH2-1ꢁ);
2.96 (br s, 2H, CH2-6ꢁꢁ); 2.51 [br s, 8H, 4 × (CH2) of
piperazine]; 2.39 (s, 3H, N-Me-piperazine), 2.09 (m,
2H, CH2-7ꢁꢁ); 2.01 (m, 2H, CH2-8ꢁꢁ). 13C-NMR (CDCl3):
δ 161.1 (C-2ꢁꢁ); 153.0 (C-9ꢁꢁ); 139.7, 130.2 (Ar-2 × C);
129.3 (Ar-2 × C); 126.0 (Ar-2 × C); 62.8 (C-1ꢁ); 53.0,
51.5 (4 × C-piperazine); 45.2 (N-Me-piperazine); 45.3
(C-5ꢁꢁ); 23.6 (C-7ꢁꢁ); 22.9 (C-6ꢁꢁ); 20.5 (C-8ꢁꢁ). Anal. calc.
for C18H25N8 (311.4): C, 69.42; H, 8.09; N, 22.49.
Found: C, 69.11; H, 7.89; N, 22.05; MS: m/z (%) (EI)
311 (65).
Preparation of 1-[(1,5-dialkyl-1H-[1,2,4]-triazol-
3-yl)benzyl]-4-methylpiperazines (8a,b,d)
To a solution of methylpiperazine (0.20 g, 2.00 mmol)
in DMF (3 mL) at ∼ −10◦C was stirred with NaH
(0.08 g, 2.00 mmol) for 15 min, followed by addition
of 6 (2.00 mmol). After stirring for 3 h at −10◦C, and
for 48 h at 25◦C, the solvent was evaporated to dry-
ness and the residue was partitioned between CH2Cl2
(50 mL) and water (25 mL) and the organic layer was
dried (Na2SO4), filtered, and evaporated to dryness.
The residue was taken by petrolium ether to give 8
as a pure solid.
1-[(6,7,8,9-Tetrahydro-5H-[1,2,4]triazolo[1,5-a]-
azepin-2-yl)benzyl]-4-methylpiperazine (8d). From
6d (0.52 g). Yield: 0.19 g (29%); mp 111–113◦C.
1H-NMR (CDCl3): δ 8.0 (d, 2H, J = 8.0 Hz, Ar); 7.35
(s, 2H, J = 8.0 Hz, Ar); 4.30 (m, 2H, CH2-10ꢁꢁ); 3.55
(s, 2H, CH2-1ꢁ); 3.02 (t, 2H, J = 6.5 Hz, CH2-6ꢁꢁ);
2.59 [br s, 8H, 4 × (CH2) of piperazine]; 2.38 (s,
3H, N-Me-piperazine); 1.95 (m, 2H, CH2-8ꢁꢁ); 1.88
(m, 2H, CH2-9ꢁꢁ); 1.78 (m, 2H, CH2-7ꢁꢁ). 13C-NMR
(CDCl3): δ 159.4 (C-2ꢁꢁ); 157.9 (C-10ꢁꢁ); 139.7, 130.6
(Ar-2 × C); 129.3 (Ar-2 × C); 126.0 (Ar-2 × C); 62.2
(C-1ꢁ); 54.9, 52.9 (4 × C-piperazine); 51.2 (C-5ꢁꢁ),
44.6 (N-Me-piperazine); 30.4 (C-7ꢁꢁ); 27.6 (C-6ꢁꢁ); 27.4
(C-9ꢁꢁ); 25.0 (C-8ꢁꢁ). Anal. calc. for C19H27N5 (325.4):
1-[(1,5-Dimethyl-1H-[1,2,4]-triazol-3-yl)benzyl]-
4-methylpiperazine (8a). From 6a (0.44 g). Yield:
0.16 g (28%); mp 170–174◦C. 1H-NMR (CDCl3): δ
8.00 (d, 2H, J 7.6 Hz, Ar); 7.42 (s, 2H, J 7.6 Hz, Ar);
3.78 (s, 3H, N-Me-triazole), 3.50 (s, 2H, CH2-1ꢁ); 2.50
[br s, 8H, 4 × (CH2) of piperazine]; 2.37 (br s, 6H,
N-Me-piperazine, C5 -Me]. 13C-NMR (CDCl3): δ 160.5
ꢁ
(C-3ꢁ); 153.0 (C-5ꢁ); 138.6, 130.3 (Ar-2 × C), 129.2
(Ar-2 × C); 126.3 (Ar-C); 125.9 (Ar-C); 61.6 (C-1ꢁ);
53.6; 52.0 (4 × C-piperazine); 43.4 (N-Me-piperazine);
ꢁ
35.2 (N-Me); 11.8 (C5 -Me). Anal. calc. for C16H23N5

32 Al-Soud et al.
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