Electric Literature of 1758-46-9,Some common heterocyclic compound, 1758-46-9, name is 2-Phenoxyethylamine, molecular formula is C8H11NO, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.
General procedure: Et3N (4.3 mmol) and 97% EtOCOCl (4.3 mmol) in dry CHCl3(25 mL) were added to a solution of the suitable carboxylic acid 24a,24b or 25 (4.3 mmol) at 0 C. After 30 min at 0 C under stirring asolution of the suitable amine (2-phenoxyethanamine, 2-(2-methoxyphenoxy)ethanamine [37], 2-(2,6-dimethoxyphenoxy)ethanamine [38], or 1-(2-methoxyphenyl)piperazine) (4.3 mmol)in dry CHCl3 (10 mL) was added and the reaction mixture was left atroom temperature for 3 h. The solution was washed with 2 N HCl and 2 N NaOH. The organic layer was dried over Na2SO4. After evaporation of the solvent the residue was purified by column chromatography eluting with cyclohexane/EtOAc (7:3). 4.1.11.1. trans-N-(2-Phenoxyethyl)-3-phenyl-1,4-dioxane-2-carboxamide (26a). This compound was prepared starting from 24a and 2-phenoxyethanamine: a solid was obtained (73% yield;mp 109-110 C). 1H NMR (CDCl3) d 3.56 (m, 2H), 3.84e4.01 (m, 6H),4.08 (d, 1H, J 9.0 Hz), 4.42 (d, 1H, J 9.0 Hz), 6.60 (br t, 1H,exchangeable with D2O), 6.86e7.38 (m, 10H). ESI/MS: m/z 328.2[M H]. Anal. Calcd for C19H21NO4: C, 69.71%; H, 6.47%; N, 4.28%.Found: C, 69.87%; H, 6.23%; N, 4.39%.
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Phenoxyethylamine, its application will become more common.
Reference:
Article; Del Bello, Fabio; Bonifazi, Alessandro; Giorgioni, Gianfabio; Quaglia, Wilma; Amantini, Consuelo; Morelli, Maria Beatrice; Santoni, Giorgio; Battiti, Francisco O.; Vistoli, Giulio; Cilia, Antonio; Piergentili, Alessandro; European Journal of Medicinal Chemistry; vol. 168; (2019); p. 461 – 473;,
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