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

CAS No.
323176-93-8
Chemical Name:
Ethyl α-(p-Methoxyphenyl)-β-(dimethylamino)propionate
Synonyms
Venlafaxine IMpurity B;Venlafaxine EP IMpurity B;Venlafaxine EP Impurity B HCl;Ethyl (2RS)-3-(Dimethylamino)-2-(4-;ethyl 3-(dimethylamino)-2-(4-methoxyphenyl);ethyl 3-(dimethylamino)-2-(4-methoxyphenyl)propanoate;Ethyl α-(p-Methoxyphenyl)-β-(dimethylamino)propionate;Ethyl α-(p-Methoxyphenyl)-β-(dimethylamino)propionate;Ethyl 3-Dimethylamino-2-(4-methoxy-phenyl)-propionate;Venlafaxine EP Impurity B (Venlafaxine Ester Impurity)
CBNumber:
CB22508656
Molecular Formula:
C14H21NO3
Molecular Weight:
251.32
MDL Number:
MFCD16293840
MOL File:
323176-93-8.mol
MSDS File:
SDS
Last updated:2023-04-23 13:52:06

Ethyl α-(p-Methoxyphenyl)-β-(dimethylamino)propionate 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
FDA UNII 20A3002JTT

Ethyl α-(p-Methoxyphenyl)-β-(dimethylamino)propionate price

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
TRC E925055 Ethylα-(p-Methoxyphenyl)-β-(dimethylamino)propionate 323176-93-8 50mg $185 2021-12-16 Buy
AK Scientific 7161CS Ethylalpha-(p-Methoxyphenyl)-beta-(dimethylamino)propionate 323176-93-8 250mg $399 2021-12-16 Buy
AK Scientific 7161CS Ethylalpha-(p-Methoxyphenyl)-beta-(dimethylamino)propionate 323176-93-8 500mg $671 2021-12-16 Buy
American Custom Chemicals Corporation CHM0293941 ALPHA-[(DIMETHYLAMINO)METHYL]-4-METHOXYBENZENEACETIC ACID ETHYL ESTER 95.00% 323176-93-8 100MG $704.55 2021-12-16 Buy
American Custom Chemicals Corporation CHM0293941 ALPHA-[(DIMETHYLAMINO)METHYL]-4-METHOXYBENZENEACETIC ACID ETHYL ESTER 95.00% 323176-93-8 1G $1593.9 2021-12-16 Buy
Product number Packaging Price Buy
E925055 50mg $185 Buy
7161CS 250mg $399 Buy
7161CS 500mg $671 Buy
CHM0293941 100MG $704.55 Buy
CHM0293941 1G $1593.9 Buy

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

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 Preparation Products And Raw materials

Raw materials

Preparation Products

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Ethyl α-(p-Methoxyphenyl)-β-(dimethylamino)propionate Ethyl (2RS)-3-(DiMethylaMino)-2-(4-Methoxyphenyl)propanoate Hydrochloride Venlafaxine EP Impurity B HCl ethyl 3-(dimethylamino)-2-(4-methoxyphenyl)propanoate α-[(DiMethylaMino)Methyl]-4-Methoxybenzeneacetic Acid Ethyl Ester Venlafaxine EP IMpurity B Venlafaxine IMpurity B D,L N,O-Didesmethylvenlafaxine (Venlafaxine Impurity B) ethyl 3-(dimethylamino)-2-(4-methoxyphenyl) Venlafaxine impurity 2/Venlafaxine EP Impurity B HCl/Ethyl α-(p-Methoxyphenyl)-β-(dimethylamino)propionate hydrochloride Ethyl (2RS)-3-(Dimethylamino)-2-(4- Benzeneacetic acid, α-[(dimethylamino)methyl]-4-methoxy-, ethyl ester Venlafaxine EP Impurity B (Venlafaxine Ester Impurity) Ethyl α-(p-Methoxyphenyl)-β-(dimethylamino)propionate Ethyl 3-(dimethylamino)-2-(4-methoxyphenyl)propanoate (Venlafaxine Impurity) Ethyl 3-Dimethylamino-2-(4-methoxy-phenyl)-propionate 323176-93-8 Intermediates & Fine Chemicals Pharmaceuticals Aromatics Impurities