ChemicalBook CAS DataBase List 2,4-DIMETHOXYPHENETHYLAMINE

2,4-DIMETHOXYPHENETHYLAMINE synthesis

6synthesis methods

Product Name:2,4-DIMETHOXYPHENETHYLAMINE
CAS Number:15806-29-8
Molecular formula:C10H15NO2
Molecular Weight:181.23

37630-19-6 Synthesis

37630-19-6
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15806-29-8
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Yield:15806-29-8 65%

Reaction Conditions:

with lithium aluminium hydride in tetrahydrofuran at 0 - 80; for 15 h;

Steps:

b) Reduction of nitro-alkenes.

General procedure: A solution of the nitro-alkene compound (1 equiv.) in anhydrous THF (10 mL/200 mg) wasadded dropwise to a suspension of LiAlH4 (4 equiv.) in anhydrous THF at 0 °C. The reactionmixture was then stirred at 80 °C overnight. After cooling to 0 °C, water (35 mL) and 4Naqueous NaOH (35 mL) were added slowly. The suspension was filtered on celite, the filtratewas partially evaporated and extracted with DCM (3 x 50 mL). The organic phases werecombined and extracted with 2N aqueous HCl (3 x 50 mL). The aqueous phases were combined,adjusted to pH = 9 with NH4OH, and extracted with DCM (3 x 50 mL). The organic phaseswere combined and washed with water (2 x 50 mL), brine (50 mL), dried over MgSO4, filteredand evaporated to yield the corresponding amine compounds. For some compounds, theobtained solid was solubilized in a minimal volume of diethyl ether and treated with a 2N HClethereal solution. Hexane was then added. After slow evaporation, a solid was formed, filteredand washed with hexane to give the hydrochloride salt. Compounds 10 and 11 were used in thenext step without further purification.-

References:

Gavara, Laurent;Verdirosa, Federica;Sevaille, Laurent;Legru, Alice;Corsica, Giuseppina;Nauton, Lionel;Sandra Mercuri, Paola;Sannio, Filomena;De Luca, Filomena;Hadjadj, Margot;Cerboni, Giulia;Vo Hoang, Yen;Licznar-Fajardo, Patricia;Galleni, Moreno;Docquier, Jean-Denis;Hernandez, Jean-Fran?ois [Bioorganic and Medicinal Chemistry,2022,vol. 72,art. no. 116964] Location in patent:supporting information