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

A. Ma. Velázquez; L. Torres; R. González; A. Valencia; L Menconi; L. Martínez; A. Ramírez; B. Camacho; S. Díaz-Barriga; R. López-Castañares; E. Angeles

doi:10.3390/M549

,

and

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.

Molbank2007, 2007(3), M549;https://doi.org/10.3390/M549

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Keywords:

4-isopropylphenol; morpholine; IR

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 (C_sp2-H Ar), 2900 (C_sp3-H).

¹H-NMR (200 MHz; CDCl₃; Me₄Si, δ_H): 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; CDCl₃δ_C): 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

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.
Biava, M.; Fioravanti, R.; Porretta, G.C.; Deidda, D.; Maullu, C.; Pompei, M. Biorg. & Med. Chem. Lett. 1999, 9, 2083–2985.
Teipel, S.; Griesar, K.; Haase, W.; Krebs, B. Inorganic Chemistry 1994, 33, 456–464.
Hodgkin, J.H. Aust. J. Chem. 1984, 37, 2371–2378.

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

Supplementary materials

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