Ethyl α-(p-Methoxyphenyl)-β-(dimethylamino)propionate
Synthesis- Product Name
- 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
- Formula Weight
- 251.32
- MOL File
- 323176-93-8.mol
Ethyl α-(p-Methoxyphenyl)-β-(dimethylamino)propionate Property
- 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
N-Bromosuccinimide Price
- Product number
- E925055
- Product name
- Ethylα-(p-Methoxyphenyl)-β-(dimethylamino)propionate
- Packaging
- 50mg
- Price
- $185
- Updated
- 2021/12/16
- Product number
- 7161CS
- Product name
- Ethylalpha-(p-Methoxyphenyl)-beta-(dimethylamino)propionate
- Packaging
- 250mg
- Price
- $399
- Updated
- 2021/12/16
- Product number
- 7161CS
- Product name
- Ethylalpha-(p-Methoxyphenyl)-beta-(dimethylamino)propionate
- Packaging
- 500mg
- Price
- $671
- Updated
- 2021/12/16
- Product number
- CHM0293941
- Product name
- ALPHA-[(DIMETHYLAMINO)METHYL]-4-METHOXYBENZENEACETIC ACID ETHYL ESTER
- Purity
- 95.00%
- Packaging
- 100MG
- Price
- $704.55
- Updated
- 2021/12/16
- Product number
- CHM0293941
- Product name
- ALPHA-[(DIMETHYLAMINO)METHYL]-4-METHOXYBENZENEACETIC ACID ETHYL ESTER
- Purity
- 95.00%
- Packaging
- 1G
- Price
- $1593.9
- Updated
- 2021/12/16
Ethyl α-(p-Methoxyphenyl)-β-(dimethylamino)propionate Chemical Properties,Usage,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).