Molbank 2007, M549

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

 

Synthesis of 4-isopropyl-bis-2,6-morpholin-4-ylmethyl-1-phenol

 

A. Ma. Vel¨¢zquez 1, L. Torres 1, R. Gonz¨¢lez 1, A. Valencia 1, I. Menconi 1, L. Mart¨ªnez 1, A. Ram¨ªrez 1,  B. Camacho 1, S. D¨ªaz-Barriga 1, R. L¨®pez-Castañares 2 and  E. Angeles 1,* 

 

1 Facultad de Estudios Superiores Cuautitl¨¢n, Universidad Nacional Aut¨®noma de M¨¦xico, M¨¦xico

2 Facultad de Qu¨ªmica de la UAEM, END OF THE AFFILIATION IS MISSING HERE

* Author to whom correspondence should be addressed. E-mail: [email protected]

 

Received: 19 January 2007 / Accepted: 24 February 2007 / Published: 30 May 2007

 

Keywords: 4-isopropylphenol, morpholine, IR

 

12


 

4-isopropyl-bis-2,6-morpholin-4-ylmethyl-1-phenol (2) was prepared from 4-isopropylphenol (1) and formaldehyde (2  eq.) and 2 eq. of morpholine. They were mixed in a round flask fitted with a condenser. The mixture was irradiated with infrared light using a medicinal infrared lamp (250 Watts) and the reaction was monitored by tlc, and after 20 minutes, the reaction was completed. The mixture was chromatographed on silica gel using solvent gradient hexane/ethyl acetate. Liquid compound, yield 70%

                                                                

IR (n cm-1; CHCl3 film) 3497 (O-H), 3023 (Csp2-H Ar), 2900 (Csp3-H).

 

1H-NMR (200 MHz; CDCl3; Me4Si, ¦ÄH): 7.31 (1H, s, OH), 7.27 ( 2H, s), 3.90 (4H, s, Ar-CH2), 3.90 (8H, m, -S-CH2- ), 2.82 (8H, m, -N-CH2- + 1H, m), 1.21 (6H, d, J=7.0 Hz). 

 

13C-NMR (50 MHz; CDCl3¦ÄC): 154.6 (C), 139.7 (C), 129.0 (CH), 118.9 (C),  65.75 (-O-CH2-), 58.13 (Ar-CH2), 51.96 (-N-CH2-), 33.08 (CH), 24.03 (CH3). 

 

FAB-MS m/z (rel%) (M+1): 335 (24%), 319, 248

 

Elemental Analysis: Calculated for C19H30O3N2 (334): C 68.23 %,  H 9.04 %,  N 8.38 %,  O 14.35 %,  found : C 68.49 %, H 9.21 %,  N 8.23 %, O 14.2 %.

 

Acknowledgements

 

The authors wish to acknowledge to PAPIIT/UNAM Projects No IN213606 and IN207705 and ALPHARMA SA de CV, by partially support this work. We would like to thank C.Barajas, F.Sotres, P.Garc¨ªa, D.Jim¨¦nez from FESC-UNAM and Rosa I.del Villar M., Oscar Yañez and Georgina Duarte from  USAI-UNAM for their skillful technical assistance and DGSCA-UNAM for their support. As a part of Project C¨¢tedra Qu¨ªmica Medicinal of FESC-UNAM.


References 
  1. Vel¨¢zquez, A.Ma.; Torres, L.A.; D¨ªaz, G.; Ram¨ªrez, A.; Hern¨¢ndez, R.; Santill¨¢n, H.; Mart¨ªnez, L.; Mart¨ªnez, I.; D¨ªaz-Barriga, S.; Abrego, V.; Balboa, M.A.; Camacho, B.; L¨®pez-Castañares, R.; Dueñas-Gonz¨¢lez, A.; Cabrera, G.; Angeles, E. ARKIVOC 2006, 2, 150-161.
  2. Biava, M.; Fioravanti, R.; Porretta, G.C.; Deidda, D.; Maullu, C.; Pompei, M. Biorg. & Med. Chem. Lett. 1999, 9, 2083-2985.
  3. Teipel, S.; Griesar, K.; Haase, W.; Krebs, B. Inorganic Chemistry 1994, 33, 456-464. 
  4. Hodgkin, J.H. Aust. J. Chem. 1984, 37, 2371-2378. 

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