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Short Note

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

by
A. Ma. Velázquez
1,
L. Torres
1,
R. González
1,
A. Valencia
1,
L Menconi
1,
L. Martínez
1,
A. Ramírez
1,
B. Camacho
1,
S. Díaz-Barriga
1,
R. López-Castañares
2 and
E. Angeles
1,*
1
Facultad de Estudios Superiores Cuautitlán, Universidad Nacional Autónoma de México, México
2
Facultad de Química de la UAEM, *END OF THE AFFILIATION IS MISSING HERE*
*
Author to whom correspondence should be addressed.
Molbank 2007, 2007(3), M549; https://doi.org/10.3390/M549
Submission received: 1 January 2007 / Revised: 24 February 2007 / Published: 30 May 2007
Versions Notes

Molbank 2007 m549 i001
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, δH): 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; CDCl3δC): 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 %.

Supplementary materials

Supplementary File 1Supplementary File 2Supplementary File 3

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.García, D.Jiménez 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 Cátedra Química Medicinal of FESC-UNAM.

References

  1. Velázquez, A.Ma.; Torres, L.A.; Díaz, G.; Ramírez, A.; Hernández, R.; Santillán, H.; Martínez, L.; Martínez, I.; Díaz-Barriga, S.; Abrego, V.; Balboa, M.A.; Camacho, B.; López-Castañares, R.; Dueñas-González, 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.

Share and Cite

MDPI and ACS Style

Velázquez, A.M.; Torres, L.; González, R.; Valencia, A.; Menconi, L.; Martínez, L.; Ramírez, A.; Camacho, B.; Díaz-Barriga, S.; López-Castañares, R.; et al. Synthesis of 4-isopropyl-bis-2,6-morpholin-4-ylmethyl-1-phenol. Molbank 2007, 2007, M549. https://doi.org/10.3390/M549

AMA Style

Velázquez AM, Torres L, González R, Valencia A, Menconi L, Martínez L, Ramírez A, Camacho B, Díaz-Barriga S, López-Castañares R, et al. Synthesis of 4-isopropyl-bis-2,6-morpholin-4-ylmethyl-1-phenol. Molbank. 2007; 2007(3):M549. https://doi.org/10.3390/M549

Chicago/Turabian Style

Velázquez, A. Ma., L. Torres, R. González, A. Valencia, L Menconi, L. Martínez, A. Ramírez, B. Camacho, S. Díaz-Barriga, R. López-Castañares, and et al. 2007. "Synthesis of 4-isopropyl-bis-2,6-morpholin-4-ylmethyl-1-phenol" Molbank 2007, no. 3: M549. https://doi.org/10.3390/M549

APA Style

Velázquez, A. M., Torres, L., González, R., Valencia, A., Menconi, L., Martínez, L., Ramírez, A., Camacho, B., Díaz-Barriga, S., López-Castañares, R., & Angeles, E. (2007). Synthesis of 4-isopropyl-bis-2,6-morpholin-4-ylmethyl-1-phenol. Molbank, 2007(3), M549. https://doi.org/10.3390/M549

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