Hostname: page-component-cd9895bd7-dzt6s Total loading time: 0 Render date: 2024-12-22T21:59:32.771Z Has data issue: false hasContentIssue false
  • English
  • Français

Synthesis and X-ray diffraction data of 1-[N-(methyl)-(3,5-dimethylphenylamino)]methylnaphthalene

Published online by Cambridge University Press:  05 March 2012

H. A. Camargo ,
N. M. Habran ,
J. A. Henao ,
D. F. Amado  and
V. V. Kouznetsov
H. A. Camargo
Affiliation:
Grupo de Investigación en Química Estructural (GIQUE), Centro de Investigación en Biomoléculas (CIBIMOL), Escuela de Química, Facultad de Ciencias, Universidad Industrial de Santander, A.A. 678, Carrera 27, Calle 9 Ciudadela Universitaria, Bucaramanga, Colombia
N. M. Habran
Affiliation:
Grupo de Investigación en Química Estructural (GIQUE), Centro de Investigación en Biomoléculas (CIBIMOL), Escuela de Química, Facultad de Ciencias, Universidad Industrial de Santander, A.A. 678, Carrera 27, Calle 9 Ciudadela Universitaria, Bucaramanga, Colombia
J. A. Henao*
Affiliation:
Grupo de Investigación en Química Estructural (GIQUE), Centro de Investigación en Biomoléculas (CIBIMOL), Escuela de Química, Facultad de Ciencias, Universidad Industrial de Santander, A.A. 678, Carrera 27, Calle 9 Ciudadela Universitaria, Bucaramanga, Colombia
D. F. Amado
Affiliation:
Laboratorio de Química Orgánica y Biomolecular (LQOBio), Centro de Investigación en Biomoléculas (CIBIMOL), Escuela de Química, Facultad de Ciencias, Universidad Industrial de Santander, A.A. 678, Carrera 27, Calle 9 Ciudadela Universitaria, Bucaramanga, Colombia
V. V. Kouznetsov
Affiliation:
Laboratorio de Química Orgánica y Biomolecular (LQOBio), Centro de Investigación en Biomoléculas (CIBIMOL), Escuela de Química, Facultad de Ciencias, Universidad Industrial de Santander, A.A. 678, Carrera 27, Calle 9 Ciudadela Universitaria, Bucaramanga, Colombia
*
a)Author to whom correspondence should be addressed. Electronic mail: jahenao@uis.edu.co
Get access Rights & Permissions [Opens in a new window]

Abstract

The 1-[N-(methyl)-(3,5-dimethylphenylamino)]methylnaphthalene (chemical formula C20H21N) was prepared by means of a condensation between alpha-naphthylaldehyde and 3,5-dimethylaniline in anhydrous ethanol to obtain the aldimine (1) which was reduced with NaBH4 to afford the 1-[N-(3,5-dimethylphenylamino)]methylnaphtalene (2), and finally, the compound (3) was obtained by N-alkylation reaction of (2) with methyl iodine (CH3I) and potassium carbonate (K2CO3) in acetone. Final compound (3) was purified by chromatographic column. The XRPD pattern for the new compound, 1-[N-(methyl)-(3,5-dimethylphenylamino)]methylnaphthalene, was obtained. This compound crystallizes in monoclinic system with space group P21/a (No. 14) and refined unit-cell parameters a=13.260(4) Å, b=15.495(5) Å, c=7.719(5) Å, β=90.19(6), and V=1586(1) Å3.

Keywords

aminesX-ray powder diffractionantifungal agents
Type
New Diffraction Data
Information
Powder Diffraction , Volume 26 , Issue 1 , March 2011 , pp. 74 - 77
Copyright
Copyright © Cambridge University Press 2011

Access options

Get access to the full version of this content by using one of the access options below. (Log in options will check for institutional or personal access. Content may require purchase if you do not have access.)

References

Boultif, A. and Loüer, D. (2004). “Indexing of powder diffraction patterns of low symmetry lattices by successive dichotomy method,” J. Appl. Crystallogr.JACGAR 37, 724–731.10.1107/S0021889804014876Google Scholar
Buhrke, V., Jenkins, R., and Smith, D. (1998). Preparation of Specimens for X-Ray Fluorescence and X-Ray Diffraction Analysis (Wiley, New York), pp. 141–142.Google Scholar
de Wolff, P. M. (1968). “A simplified criterion for the reliability of a powder pattern,” J. Appl. Crystallogr.JACGAR 1, 108–113.10.1107/S002188986800508XGoogle Scholar
Ghannoum, A. and Rice, A. B. (1999). “Antifungal agents: Mode of action, mechanism of resistance, and correlation of these mechanisms with bacterial resistance,” Clin. Microbiol. Rev.ZZZZZZ 12, 501–517.Google Scholar
Kouznetsov, V. V., Vargas, L. Y., Sortino, M., Vásquez, Y., Gupta, M. D., Freile, M., Enriz, R. D., and Zacchino, S. A. (2008). “Antifungal and cytotoxic activities of some N-substituted aniline derivates bearning a hetaryl fragment,” Bioorg. Med. Chem.BMECEP 16, 794–809.10.1016/j.bmc.2007.10.034CrossRefGoogle Scholar
Laugier, J. and Bochu, B. (2002). “LMGP-suite suite of programs for the interpretation of X-ray. Experiments,” CHEKCELL, Computer software, ENSP/Laboratoire des Matériaux et du Génie Physique, BP 46, 38042 Saint Martin d’Hères, France, ⟨http://www.inpg.fr/LMGP⟩ and ⟨http://www.ccp14.ac.uk/tutorial/lmgp/⟩.Google Scholar
Miguell, A. D., Hubberd, C. R., and Stalick, J. K. (1981). “NBS* AIDS80: A FORTRAN program for crystallographic data evaluation,” NBS Tech. NoteNBTNAE 1141.Google Scholar
Rachinger, W. A. (1948). “A correction for the α 1α 2 doublet in the measurement of widths of X-ray diffraction lines,” J. Sci. Instrum.JSINAY 25, 254–255.10.1088/0950-7671/25/7/125Google Scholar
Ryder, N. S., Wagner, S., and Leitner, I. (1998). “In vitro activities of terbinafine against cutaneous isolates of Candida albicans and other pathogenic yeasts,” Antimicrob. Agents Chemother.AMACCQ 42, 1057–1061.Google Scholar
Saviztky, A. and Golay, M. J. (1964). “Smoothing and differentiation of data by simplified least squares procedures,” Anal. Chem.ANCHAM 36, 1627–1639.10.1021/ac60214a047Google Scholar
Schäfer-Korting, M., Schoellmann, C., and Korting, H. C. (2008). “Fungicidal activity plus reservoir effect allows short treatment courses with terbinafine in tinea pedis,” Skin Pharmacol. Appl. Skin Physiol.ZZZZZZ 21, 203–210.10.1159/000135636Google Scholar
Smith, G. S. and Snyder, R. L. (1979). “F N: A criterion for rating powder diffraction patterns and evaluating the reliability of powder-pattern indexing,” J. Appl. Crystallogr.JACGAR 12, 60–65.10.1107/S002188987901178XGoogle Scholar
Sonneveld, E. J. and Visser, J. W. (1975). “Automatic collection of powder diffraction data from photographs,” J. Appl. Crystallogr.JACGAR 8, 1–7.10.1107/S0021889875009417Google Scholar
Vargas M., L. Y., Castelli, M. V., Kouznetsov, V. V., Urbina, J. M., López, S. N., Sortino, M., Enriz, R. D., Ribas, J. C., and Zacchino, S. A. (2003). “In vitro antifungal activity of new series of homoallylamines and related compounds with inhibitory properties of the synthesis of fungal cell wall polymers,” Bioorg. Med. Chem.BMECEP 11, 1531–1550.10.1016/S0968-0896(02)00605-3Google Scholar