Molbank 2006, M496

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

 

3-[Benzyl-(1,5-dimethyl-1H-pyrazol-3-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.

 

 

To a mixture of 3-chloromethyl-1,5-dimethylpyrazole 1 [3] (0.51g, 3.53mmol) and sodium carbonate (1.5g, 14.12mmol) in 32 mL of acetonitrile was added slowly 3-(benzylamino)propionitrile 2 [4] (0.56g, 3.53mmol). The mixture was stirred at room temperature for four days. The solid material (Na2CO3, NaCl) was filtered and the filtrate was concentrated under reduced pressure to give the title compound 3 as yellow oil (85%).

 

1H-NMR (300 MHz, CDCl3): δ= 7.24-7.40(CHarom, 5H, m) ; 6.02(CHpyr, 1H, s) ; 3.68(N-CH3, 3H, s);  3.66(N-CH2-C, 2H, s);  3.62 (C6H5-CH2, 2H, s);  2.76-2.81(CH2-CH2-CN, 2H,  t,  J = 7.66 Hz); 2.42-2.47 ( N-CH2, t, J = 7.66 Hz); 2.24 ( CH3, 3H, s).

 

13C-NMR (CDCl3, 75 MHz): δ= 147.91(j); 139.85(l); 138.93(e); 129.29 and 129.19 (f); 128.79(g); 127.65(h); 119.37(a); 105.64(k); 58.67(d); 51.22(i); 48.82(c); 36.28(n); 16.63(b); 11.64(m).

 

EI-MS (70 eV, m/z): 228; 173 (2.4); 119; 95(4.7); 91 (37.3).

 

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. Fifani, J.; Ramdani, A.; Tarrago, G. Nouv. J. Chem., 1977, 1, 521.  

4. 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.

 

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