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Reductive Alkylation of Acetophenone with Aniline
Published in Mike G. Scaros, Michael L. Prunier, Catalysis of Organic Reactions, 2017
R.E. Malz, E.H. Jancis, M.P. Reynolds, S.T. O’Leary
A more practical and possibly commercial method of preparing benzylamines, specifically phenylbenzylamines, and the compound of our primary interest N-phenyl-α-methyibenzylamine, calls for reductive alkylation of amines with acetophenone in the presence of hydrogen and a suitable catalyst. Numerous literature sources review and detail examples of reductive alkylation of amines and carbonyl compounds.7,8,9&10 Specific examples of using acetophenone with liquid ammonia to produce benzylamine report yields of 15-52%.11 Additionally, one could react acetophenone and an amine to produce the benzalimine for isolation and subsequent hydrogenation or chemical reduction to benzylamines. Reported yields for this route to produce benzylaniline are 73-100%12. Freifelder reported13 acetophenone reductively alkylated with 2-aminoethanol using PtO2 or prereduced Pt gave an 80% yield of N-(α-methyl benzyl) ethanolamine; with 3,3-diphenylpropylamine a gave 80.5% yield of N-(α-methyl benzyl)-3,3-diphenylpropylamine.
Identification of transformation products during Doxylamine chloramination for NDMA mitigation
Published in Environmental Technology, 2022
B. Coskun, N. Bilgin-Saritas, E. Aydin, E. Pehlivanoglu-Mantas
Although currently there are no studies on the pathways for the chloramination of Doxylamine, several studies focused on the investigation of NDMA formation pathways from model compounds such as ranitidine, dimethylamine, trimethylamine, chlorpheniramine, chlortetracycline hydrochloride, benzylamine, dimethylaniline, choline, poly (diallydimethylammonium chloride), polyquaternium-7, polyacrylamide and cocoamidopropyl betaine [40–43]. As suggested for Group 1 compounds of Doxylamine chloramination, hydrolysis was shown to be an important reaction for other NDMA precursors [54, 53]. Hydrolysis of monochloramine provides decomposition of ranitidine and increases the formation of NDMA in water media [32]. Also, hydrolysis of amines might be an important step during formation of NDMA [56]. The presence of non-protonated amines from NDMA precursors are important for NDMA formation and hence lowering the pH may decrease NDMA concentration during chloramination of Ranitidine and Sumatriptan [34]. However, it is important to note that the pH also might shift the speciation of mono vs. dichloramines.
Synthesis and evaluation of Zn(II) dithiocarbamate complexes as potential antibacterial, antibiofilm, and antitumor agents
Published in Journal of Coordination Chemistry, 2019
Vinay Kumar Maurya, Ashish Kumar Singh, Ravi Pratap Singh, Shivangi Yadav, Krishna Kumar, Pradyot Prakash, Lal Bahadur Prasad
In preparation of dithiocarbamate ligands, the secondary amines were synthesized by the reaction of 4-isopropyl-benzaldehyde (0.148 g, 1 mmol) and benzylamine (0.108 g, 1 mmol) for KL1; benzaldehyde (0.102 g, 1 mmol) and ethylamine (0.056 g, 1 mmol) for KL2; 4-isopropyl-benzaldehyde (0.148 g, 1 mmol) and 4-methoxybenzylamine (0.137 g, 1 mmol) for KL3; 4-methyl-benzeldehyde (0.118 g, 1 mmol) and ethylamine (0.056 g, 1 mmol) for KL4 dissolved in 15 mL ethanol with 8 h refluxing at 70–80 °C [26]. The obtained reaction mixture(s) contain Schiff base, which was then placed in ice-cold conditions. To reduce the obtained Schiff base solution, methanolic solution of NaBH4 was added with constant stirring and the obtained product was extracted with dichloromethane (45 mL), with subsequent washing with distilled water five times (25 mL). The oily yellow mixture was extracted on a rotary evaporator. The potassium salts of KL1–KL4 dithiocarbamate ligands were made by the reaction of KOH (0.056 g, 1 mmol) and carbon disulfide (0.076 g, 1 mmol) with relevant secondary amine (25 mL THF solvent) prepared as given in Scheme 1 under ice-cold conditions and maintained temperature below 8 °C. The final product was further stirred for 5 h at room temperature and the solvent was removed over a rotary evaporator. The obtained product was washed thrice with ether to yield a pale yellow solid product.