Skip to main content

Synthesis and Characterization of a Butenafine Analogue | Chapter 07 | Theory and Applications of Chemistry Vol. 3

Aims: The study aims: (I) To synthesise N-(4-(tert-butyl) benzyl)-1-(4-tert-butyl) phenyl)-N-methyl methanaminium chloride, an  analogue  of butenafine from tertiary-butyl benzyl derivatives, (II) to compare the solvent actions of Tetrahydrofuran (THF), acetonitrile, methanol and 1,2-dichloroethane (DCE), and the reducing efficiencies of NaBH4 and sodium triacetoxyborohydride (STAB) during the synthesis.

Study Design: The study involved laboratory experiments leading to the synthesis of the target compound by varying the non-aqueous solvents used, the reducing agent and the temperature of the operations. Silica chloride catalyst was used to speed up the reaction in one of the syntheses and in each synthesis, Thin Layer Chromatography was used to monitor the progress of the reaction. The time taken by each reaction and the yield were used as the basis for determining the solvent action and the reducing efficiency. 

Place and Duration of Study: M.Sc. Access controlled Teaching Laboratory, School of Chemistry, Newcastle University, New castle upon Tyne, United Kingdom from June to August 2012.

Methodology: Reductive amination was carried out by reacting 4-tert-butylbenzaldehyde and 4-tert-butylbenzylamine, using the direct and then the indirect approaches. This was followed by methylation using the Eschweiler-Clarke reaction in each of the two approaches. The time taken by each reaction was monitored and the product of each approach was characterised by EIS-MS, 1H NMR, 13C NMR and FTIR.

Results: 1,2-dichloroethane gave the best solvent action at 40°C (Yield: 75%) and NaBH4  gave the best-reducing action with silica chloride catalyst at 25°C (Yield: 50%). At the end of each synthesis,  in all obtained  products, 1H NMR spectrum gave a single peak of 18 hydrogen atoms at 1.3 -1.5 ppm for the existence of 6 methyl groups in the two tertiary-butyl substituents, the 13C NMR spectrum also showed a peak at  31-32 ppm for the six methyl carbon atoms in the two tertiary-butyl substituents, the FTIR spectrum showed  a strong band at  2460 cm-1 for the presence of a tertiary ammonium ion and finally the EIS-MS gave  a mass to charge ratio of 324.2693 as a confirmation of the relative molecular mass of the compound.

Conclusion: The target compound can be synthesised by both direct and the indirect approaches of reductive amination in any of the solvents tested with/without a catalyst at room or elevated temperature using NaBH4 or STAB as a reducing agent but the best solvent action can be achieved with DCE at 40°C and the best-reducing action can be achieved with NaBH4 in the presence of silica chloride.

Author(s) Details

M. A. Muhammad
Department of Chemistry, Ibrahim Badamasi Babangida University, P.M.B 11, Lapai, Niger State, Nigeria.

A. M. Jimoh
Department of Chemistry, Ibrahim Badamasi Babangida University, P.M.B 11, Lapai, Niger State, Nigeria.

A. Awwal
Department of Chemistry, Ibrahim Badamasi Babangida University, P.M.B 11, Lapai, Niger State, Nigeria.

View Volume: http://bp.bookpi.org/index.php/bpi/catalog/book/104

Comments

Popular posts from this blog

A Prospective Study about Safety and Efficacy of Perioperative Lidocaine Infusion | Chapter 09 | New Horizons in Medicine and Medical Research Vol. 8

 Opioids cause clinically significant side effects such as respiratory depression, immunosuppression, muscle rigidity, negative inotropism, nausea, vomiting, hyperalgesia, urine retention, postoperative ileus, and drowsiness. Perioperative opioids are a major contributor to the United States' and other countries' opioid epidemics. Non-opioid analgesics, particularly lidocaine, are becoming more common for perioperative use as a result of this. A total of 185 adult patients were randomly assigned to one of two groups: control group I (105 patients) [fentanyl group] or group ii (80 patients) [opioid-free anaesthesia group]. Lidocaine 1.5 mg/kg bolus followed by 1.5 mg/kg/h infusion intraoperatively, and 1.5-2 mg/kg/h infusion for 2-8 hours postoperatively were given to patients in both groups at anaesthetic induction. Intraoperatively, both groups received analgesic adjuvants such as diclofenac 75 mg, paracetamol 1 gm, and mgso4 30-50 mg/kg. If the mean arterial pressure (map)

A Brief Study of Middleware Technologies: Programming Applications and Management Systems | Chapter 15 | Novel Research Aspects in Mathematical and Computer Science Vol. 1

  Many platforms, services, applications, hardware, and operating systems are connected through the middleware layer. Because the middleware layer abstracts much low-level complexity and makes applications and software systems portable, it allows disparate systems to interface and function together in harmony. Middleware technologies enable software engineers to swiftly construct software systems and applications, allowing developers to focus on more important tasks. This chapter examines several types of middleware systems and discusses middleware capabilities, middleware operation, middleware's function in cloud-based systems, and the best middleware platforms to use. Middleware systems are widely utilised and can be found in practically any software system or application. Middleware programmes provide as a link between many sorts of systems and protocols. They serve as a mechanism for various systems. To successfully exchange information, it runs on a variety of operating system

Ethnopharmacological Survey among Traditional Medicine Practitioners in Abidjan (Côte d'Ivoire) for the Management of Pathologies such as Malaria, ENT Diseases, Diarrhea, Typhoid Fever and Anemia | Chapter 05 | New Horizons in Medicine and Medical Research Vol. 8

 Traditional Medicine Practitioners (TMPs) of Côte d'Ivoire are familiar with the therapeutic herbs. Medicinal plants have been shown to be useful in the treatment of common diseases such as malaria (KROA, 2004) and diabetes (N'GUESSAN et al, 2013) in several studies and scientific study. In the Abidjan District, the current policy is to integrate traditional medicine and pharmacopoeia into the national health system in order to improve population health coverage, particularly in the management of commonly encountered diseases such as malaria, ENT diseases, diarrhoea, typhoid fever, and anaemia. This research aims to increase the use of traditional medicine and pharmacopoeia in the national health system. Over the course of three months, fifty (50) PMTs in the District of Abidjan participated in this study. Plant therapists accounted for 30 of the 50 PMTs polled at the end of the study, or 60%. Traditional medicine centres use 61 types of medicinal plants from 36 famili