ChemicalBook CAS DataBase List 2-(4-methoxyphenoxy)-N,N-dimethylethanamine

2-(4-methoxyphenoxy)-N,N-dimethylethanamine synthesis

7synthesis methods

Product Name:2-(4-methoxyphenoxy)-N,N-dimethylethanamine
CAS Number:51344-12-8
Molecular formula:C11H17NO2
Molecular Weight:195.26

Carbonic acid, 2-(dimethylamino)ethyl methyl ester

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150-76-5 Synthesis

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2-(4-methoxyphenoxy)-N,N-dimethylethanamine

51344-12-8
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Yield:51344-12-8 96%

Reaction Conditions:

in acetonitrile at 220; for 0.116667 h;Sealed tube;Microwave irradiation;Solvent;

Steps:

Reaction between 2-(dimethylamino)ethyl methyl carbonate 2 and phenol in ACN - Table 1, No.7

General procedure: Phenol (0.060 g, 0.637 mmol) was dissolved in ACN (3 mL) at room temperature in a 10 mL CEM pressure vessel equipped with a stirrer bar. 2-(Dimethylamino)ethyl methyl carbonate 2 (0.140 g, 0.955 mmol) was added and the vial was sealed and heated in a CEM Discover microwave synthesizer to 220 °C for 7 min. After cooling, a sample of the crude material was analysed by HPLC to define conversion and selectivity. Then, the reaction mixture was concentrated via rotavapor and it was purified via liquid-liquid extraction (EtOAc 50 mL / NaOH 5% aqueous solution 50 mL x 3). The organic phase was dried with sodium sulphate, filtered and concentrated under vacuum. The pure compound was isolated as a brown oil in 95% yield (0.100 g). Characterization of compound 3 was consistent with one reported in the literature.²

References:

Viviano, Monica;Trapasso, Giacomo;Annatelli, Mattia;Milite, Ciro;Castellano, Sabrina;Aricò, Fabio [Synthesis,2022,vol. 54,# 11,p. 2595 - 2603] Location in patent:supporting information