Ethyl α-(p-Methoxyphenyl)-β-(dimethylamino)propionate Chemical Properties

Boiling point:

337.9±42.0 °C(Predicted)

Density 

1.045±0.06 g/cm3(Predicted)

storage temp. 

Refrigerator

solubility 

Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)

form 

Oil

pka

8.61±0.28(Predicted)

color 

Pale Brown to Light Brown

Ethyl α-(p-Methoxyphenyl)-β-(dimethylamino)propionate Usage And Synthesis

Synthesis

A mixture of ethyl p-methoxyphenylacetate (4 g, 20.62 mmol), paraformaldehyde (1.05 g, 35.0 mmol) and TBAI (0.381 g, 1.03 mmol) was heated in PhMe (16 ml) at 80-85 ºC for 3.5 hours. The reaction mixture was allowed to cool. Then, a solution of Me2NH in THF was added to the reaction mixture at 0 ºC in the presence of catalytic FeCl3 (0.160 g, 0.001 mol) and stirred for 45 minutes. After completion of the reaction, 100 ml water was added to the reaction mixture and aqueous layer was acidified with conc. HCl (pH = 2). Aqueous layer was washed with DCM (3x 50 ml) and made alkaline (pH = 8) using 5% NaOH solution, extracted with DCM (3x 50 ml), washed with water, brine, dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. Column chromatographic purification over silca gel (0.5% MeOH in CHCl3) furnished aminoester 65 as a thick colourless oil (3.08 g). When the reaction was carried out without catalyst, it took 48 hours for completetion.

Uses

Ethyl α-(p-Methoxyphenyl)-β-(dimethylamino)propionate (Venlafaxine EP Impurity B) is an impurity of Venlafaxine (impurity B).

Ethyl α-(p-Methoxyphenyl)-β-(dimethylamino)propionate(323176-93-8)Related Product Information

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