Molbank 2006, M495

http://www.mdpi.org/molbank/

 

3-[Benzyl-(3,5-dimethyl-pyrazol-1-ylmethyl)-amino]-propionitrile

 

Leila Herrag,1,2*  Rachid Touzani,1,3  Abdelkrim Ramdani1 and Belkheir Hammouti2

 

1 Laboratoire de Chimie Organique Physique, Département de Chimie , Faculté des Sciences , Université Mohammed Premier , B.P. 524, 60000 Oujda , Maroc.

2Laboratoire de Chimie des Eaux et Corrosion, Département de Chimie, Faculté des  Sciences,  B.P. 717, Oujda, Maroc.

3 Université Mohammed Premier, Faculté Pluridisciplinaire de Nador B.P. 300, 62700 Selouane, Nador, Maroc

E-mail: [email protected]

*Author to whom correspondence should be addressed

 

Received: 19 July 2006 / Accepted: 31 July 2006 / Published: 1 September 2006

 

Keywords: pyrazole; propionitrile and tridentate nitrogen ligand.

 

The products of aza-type Michael addition, i.e., β-amino carbonyl compounds and their derivatives, are often used as peptide analogs or precursors of optically active amino acids, amino alcohols, diamines, and lactams [1]. Moreover, β-amino carbonyl functionalities are ubiquitous motifs in natural products such as alkaloids and polyketides [2]. Herein, we report the synthesis of new product using aza-type Michael reactions under mild conditions.

 

 

A mixture of 3-(benzylamino)propionitrile 1 [3] (1g, 6.25mmol) and  1-hydroxymethyl-3,5-dimethyl pyrazole 2 [4] (0.79g , 6.25 mmol) in 20 ml of acetonitrile was stirred at room temperature for four days, then the mixture was dried with Na2SO4 and filtered.  The solvent was evaporated under reduced pressure. The product 3 obtained with a 97% yield as yellow oil.

 

1H-NMR (300 MHz, CDCl3): δ= 7.31-7.37 (CHarom, 5H, m); 4.80 ( N-CH2-N, 2H, s); 3.75 (C6H5-CH2 ,2H, s); 2.98-3.02 (CH2-CH2-CN, 2H,  t, J = 7.66 Hz) ; 2.31-2.35 ( N-CH2, t, J = 7.66 Hz); 2.22 ( CH3, 3H, s) and 2.15 ( CH3, 3H, s).

 

13C-NMR (CDCl3, 75 MHz): δ= 148.18 (l); 140.5 (j); 138.12 (e); 129.11 (f); 128.99 (g); 128.03 (h); 119.27 (a); 106.35 (k); 66.56 (i); 56.94 (d); 48.24 (c); 17.23 (b); 13.95 (m); 11.46 (n).

 

EI-MS (70 eV, m/z): 173 (17.4); 171; 119; 95; 91 (100).

 

References:

1. Fustero, S.; Pina, B.; Salavert, E.; Navarro, A.; Ramirez de Arellano, M. C.; Fuentes, A. S. J. Org. Chem. 2002, 67, 4667.

2. Arend, M.; Westermann, B.; Risch, N. Angew. Chem., Int. Ed 1998, 37, 1045.

3. a) Xu, L.W.; Li, L.; Xia, C.-G. Helvetica Chimica Acta, 2004, 87, 1522. b) Azizi, N.; Saidi, M. R.  Tetrahedron, 2004, 60, 383.

4. Dvoretzky I.; Richte G. H. J. Org. Chem., 1950, 15, 1285.

 

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