The Study of the Reaction of Morpholine with 4-Bromobenzaldehyde in the Presence and Absence of Copper(I) Iodide
Abstract
This short communication reports the comparison of the reaction between morpholine with 4-bromobenzaldehyde in the condition with and without copper (I) iodide (CuI) as the catalyst. The reactions were
carried out at 110 ºC under reflux condition for 24 hours, and the products were analysed using gas
chromatography mass spectroscopy (GCMS). The GC results showed that the conversion of the product without
CuI catalyst was higher than the reaction with catalyst under the same condition. Side product also was observed
in the reaction without catalyst, which is because the morpholine was actually also attacked to the carbon in the
carbonyl group of 4-bromobenzaldehyde to produce 4-bromobenzoic acid morpholide.
References
Basu, B., Das, S., & Mandal, B. (2007). Role of copper in catalyzing aryl and heteroarylnitrogen (-or -oxygen) bond formation under ligand-free and solvent-free conditions. Indian Journal of Chemistry, 47B: 1701-1706.
Beletskaya, I.P. & Cheprakov, A.V. (2004). Copper in cross-coupling reactions the postullmann chemistry. Journal of Coordination Chemistry, 248: 2337-2364.
https://doi.org/10.1016/j.ccr.2004.09.014
Hillier, A.C., Grasa, G.A., Viciu, M.S., Lee, H. M., Yang, C., & Nolan, S.P. (2002). Catalytic cross-coupling reactions mediated by palladium/nucleophilic carbene systems. Journal of Organometallic Chemistry, 653: 69-82.
https://doi.org/10.1016/S0022-328X(02)01154-3
Lundgren, R.J., Kumankumah, A.S., & Stradiotto, M. (2010). A highly versatile catalyst system for the cross-coupling of aryl chlorides and amines. Journal of European Chemical, 16:1983-1991.
https://doi.org/10.1002/chem.200902316
Mjos, K. (1978). Cyclic amines. ln: Mark, H.E., Othmer, D.E., Overberger, C.G., Seaborg, G.T., & Grayson,M., eds, KÙk-Othmer Encyclopedia of Chemical Technology, 3rd ed., Vol. 2. New York: John Wiley & Sons. Pp 295-308.
Sperotto, E., Gerard, P.M., Klink, V., De Vries, J.G., & Koten, G.V. (2010a). C-N coupling of nitrogen nucleophiles with aryl and heteroaryl bromides using aminoarenethiolato-copper (I) (pre-) catalyst. Journal of Tetrahedron, 66: 3478-3484.
https://doi.org/10.1016/j.tet.2010.03.040
Sperotto, E., Gerard, P.M., Klink, V., De Vries, J.G., & Koten, G.V. (2010b). The mechanism of the modified ullmann reaction. Dalton Transactions, 39: 10338-10351.
Copyright (c) 2016 Borneo Journal of Resource Science and Technology
This work is licensed under a Creative Commons Attribution-NonCommercial 4.0 International License.
Copyright Transfer Statement for Journal
1) In signing this statement, the author(s) grant UNIMAS Publisher an exclusive license to publish their original research papers. The author(s) also grant UNIMAS Publisher permission to reproduce, recreate, translate, extract or summarize, and to distribute and display in any forms, formats, and media. The author(s) can reuse their papers in their future printed work without first requiring permission from UNIMAS Publisher, provided that the author(s) acknowledge and reference publication in the Journal.
2) For open access articles, the author(s) agree that their articles published under UNIMAS Publisher are distributed under the terms of the CC-BY-NC-SA (Creative Commons Attribution-Non Commercial-Share Alike 4.0 International License) which permits unrestricted use, distribution, and reproduction in any medium, for non-commercial purposes, provided the original work of the author(s) is properly cited.
3) For subscription articles, the author(s) agree that UNIMAS Publisher holds copyright, or an exclusive license to publish. Readers or users may view, download, print, and copy the content, for academic purposes, subject to the following conditions of use: (a) any reuse of materials is subject to permission from UNIMAS Publisher; (b) archived materials may only be used for academic research; (c) archived materials may not be used for commercial purposes, which include but not limited to monetary compensation by means of sale, resale, license, transfer of copyright, loan, etc.; and (d) archived materials may not be re-published in any part, either in print or online.
4) The author(s) is/are responsible to ensure his or her or their submitted work is original and does not infringe any existing copyright, trademark, patent, statutory right, or propriety right of others. Corresponding author(s) has (have) obtained permission from all co-authors prior to submission to the journal. Upon submission of the manuscript, the author(s) agree that no similar work has been or will be submitted or published elsewhere in any language. If submitted manuscript includes materials from others, the authors have obtained the permission from the copyright owners.
5) In signing this statement, the author(s) declare(s) that the researches in which they have conducted are in compliance with the current laws of the respective country and UNIMAS Journal Publication Ethics Policy. Any experimentation or research involving human or the use of animal samples must obtain approval from Human or Animal Ethics Committee in their respective institutions. The author(s) agree and understand that UNIMAS Publisher is not responsible for any compensational claims or failure caused by the author(s) in fulfilling the above-mentioned requirements. The author(s) must accept the responsibility for releasing their materials upon request by Chief Editor or UNIMAS Publisher.
6) The author(s) should have participated sufficiently in the work and ensured the appropriateness of the content of the article. The author(s) should also agree that he or she has no commercial attachments (e.g. patent or license arrangement, equity interest, consultancies, etc.) that might pose any conflict of interest with the submitted manuscript. The author(s) also agree to make any relevant materials and data available upon request by the editor or UNIMAS Publisher.
