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ChemicalBook--->CAS DataBase List--->323176-93-8

323176-93-8

323176-93-8 Structure

323176-93-8 Structure
IdentificationBack Directory
[Name]

Ethyl α-(p-Methoxyphenyl)-β-(dimethylamino)propionate
[CAS]

323176-93-8
[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 α-(p-Methoxyphenyl)-β-(dimethylamino)propionate
ethyl 3-(dimethylamino)-2-(4-methoxyphenyl)propanoate
Ethyl α-(p-Methoxyphenyl)-β-(dimethylamino)propionate
Venlafaxine EP Impurity B (Venlafaxine Ester Impurity)
D,L N,O-Didesmethylvenlafaxine (Venlafaxine Impurity B)
α-[(DiMethylaMino)Methyl]-4-Methoxybenzeneacetic Acid Ethyl Ester
Benzeneacetic acid, α-[(dimethylamino)methyl]-4-methoxy-, ethyl ester
Ethyl (2RS)-3-(DiMethylaMino)-2-(4-Methoxyphenyl)propanoate Hydrochloride
Venlafaxine impurity 2/Venlafaxine EP Impurity B HCl/Ethyl α-(p-Methoxyphenyl)-β-(dimethylamino)propionate hydrochloride
[Molecular Formula]

C14H21NO3
[MOL File]

323176-93-8.mol
[Molecular Weight]

251.32
Chemical PropertiesBack Directory
[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
Questions And AnswerBack Directory
[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.
Hazard InformationBack Directory
[Uses]

An impurity of Venlafaxine (impurity B).
[Uses]

Ethyl α-(p-Methoxyphenyl)-β-(dimethylamino)propionate (Venlafaxine EP Impurity B) is an impurity of Venlafaxine (impurity B).
Spectrum DetailBack Directory
[Spectrum Detail]

Ethyl α-(p-Methoxyphenyl)-β-(dimethylamino)propionate(323176-93-8)1HNMR
Ethyl α-(p-Methoxyphenyl)-β-(dimethylamino)propionate(323176-93-8)13CNMR
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