Molbank 2005, M451

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Synthesis of New bis-Bidentate Nitrogen Ligand: 1,4-bis[(3,5-dimethyl-1H-pyrazol-1-yl)methyl]piperazine

 

Abdeljalil EL FATMI,a Maria DAOUDI,a,* Najib BEN LARBI,a Abdelali KERBAL,a Mohamed FILALI BABA,b Brahim EL BALI,b Michael BOLTE,c Mohamed MCHICH,d Taibi BEN-HADDA d,*

 

a Laboratoire de Chimie Organique, D¨¦partement de Chimie, Facult¨¦ des Sciences Dhar El Mehraz, F¨¨s, Morocco

b Laboratoire d'Analyses, d'Essais et d'Environnement (LAEE), D¨¦partement de Chimie, Facult¨¦ des Sciences Dhar Mehraz, Universit¨¦ Sidi Mohamed Ben Abdellah, 30000 F¨¨s, Morocco

c Institut fur Organische Chemie, J. W. Goethe-Universitat Frankfurt, Marie-Curie-Str. 11, 60439 Frankfurt/Main, Germany

d Laboratoire d¡¯activation mol¨¦culaire, Department of Chemistry, Faculty of Sciences, 60000 Oujda, Morocco.

e-mail: [email protected] and [email protected]

 

Received: 15 July 2005 / Accepted: 24 September 2005 / Published: 12 December 2005

 

Keywords: bis-Bidentate N Ligand - Pyrazole ¨C Amonium/ alcohol condensation.

 

 

The product 2 was prepared by the addition of piperazine (C4H10N2) to 1 [1] according to the reported procedure [2]. To a solution of the substituted hydroxymethylpyrazole 1 (1.26 g, 10 mmol) in acetonitrile (50 ml) was added piperazine (0.95 g, 5 mmol) and the mixture was stirred. The stirring was continued at room temperature for 4 days. The solvent was evaporated under reduced pressure. The solid was cristallised in ethanol to afford 2 as a white solid (2.31 g, 76%).

 

Melting point: 158-160¡ãC.

 

IR (KBr, cm¨C 1): 2270 (CH); 1650 (C=C, C=N).

 

1H- NMR (60 MHz, CDCl3): ¦Ä= 5.8 (s, 2H, Pyrazol, H4,4'); 4.6 (s, 4H, 2NCH2N); 2.6 (s, 8H, 4CH2-N); 2.30 (s, 12H, 4CH3).  

 

13C-NMR (300MHz, D2O): ¦Ä= 9.64 (Pz-CH3); 12.12 (Pz-CH3); 69.4 (Pz-CH2-N); 81.75 (N-CH2_CH2_N); 106.38(PzC-H); 141.66 (PzC=N); 149.94(PzC-N).

 

EI-MS (m/z; %): Calculated for C16H26N6: 302.418. Found: 303[M+1]; 109; 95.

 

Acknowledgments

We are indebted to the "Projet Global d¡¯Universit¨¦ Mohamed Premier" for financial support.

 

References

1. Dvoretzky, I.; Richter, G.H., J.Org.Chem., 1950, 15, 1285.

2. Sheu, S-C; Tien, M-J.; Cheng, M-C.; Ho, T-I.; Peng, S-M. And Lin, Y-C., J. Chem. Soc. Dalton Trans, 1995, 3503-3510. 

 

Sample Availability: Available from the authors and MDPI.

 

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