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

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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

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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

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Hazard and Precautionary Statements (GHS)

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N-Bromosuccinimide Price

TRC

Product number: E925055
Product name: Ethylα-(p-Methoxyphenyl)-β-(dimethylamino)propionate
Packaging: 50mg
Price: $185
Updated: 2021/12/16

AK Scientific

Product number: 7161CS
Product name: Ethylalpha-(p-Methoxyphenyl)-beta-(dimethylamino)propionate
Packaging: 250mg
Price: $399
Updated: 2021/12/16

AK Scientific

Product number: 7161CS
Product name: Ethylalpha-(p-Methoxyphenyl)-beta-(dimethylamino)propionate
Packaging: 500mg
Price: $671
Updated: 2021/12/16

American Custom Chemicals Corporation

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

American Custom Chemicals Corporation

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

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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).

Ethyl α-(p-Methoxyphenyl)-β-(dimethylamino)propionate Preparation Products And Raw materials

Raw materials

Preparation Products

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323176-93-8, Ethyl α-(p-Methoxyphenyl)-β-(dimethylamino)propionateRelated Search:

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

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Venlafaxine EP Impurity B HCl

ethyl 3-(dimethylamino)-2-(4-methoxyphenyl)propanoate

α-[(DiMethylaMino)Methyl]-4-Methoxybenzeneacetic Acid Ethyl Ester

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Venlafaxine IMpurity B

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

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