323176-93-8 Usage
Description
Ethyl α-(p-Methoxyphenyl)-β-(dimethylamino)propionate, also known as Venlafaxine EP Impurity B, is an organic compound that is an impurity found in Venlafaxine, a widely prescribed antidepressant medication. It is characterized by its unique chemical structure, which includes a p-methoxyphenyl group and a dimethylamino group attached to a propionate backbone.
Uses
Used in Pharmaceutical Industry:
Ethyl α-(p-Methoxyphenyl)-β-(dimethylamino)propionate is used as an impurity in Venlafaxine for [application reason]. It is important to monitor and control the levels of this impurity in Venlafaxine to ensure the safety and efficacy of the medication. The presence of impurities can affect the quality, stability, and performance of the drug, so their identification and management are crucial in the pharmaceutical manufacturing process.
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.
Check Digit Verification of cas no
The CAS Registry Mumber 323176-93-8 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 3,2,3,1,7 and 6 respectively; the second part has 2 digits, 9 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 323176-93:
(8*3)+(7*2)+(6*3)+(5*1)+(4*7)+(3*6)+(2*9)+(1*3)=128
128 % 10 = 8
So 323176-93-8 is a valid CAS Registry Number.
323176-93-8Relevant articles and documents
Practical synthesis of (±)-venlafaxine
Chavan, Subhash P.,Khobragade, Dushant A.,Thakkar, Mahesh,Kalkote, Uttam R.
, p. 3901 - 3906 (2007)
A practical total synthesis of antidepressant (±)-venlafaxine is disclosed. Copyright Taylor & Francis Group, LLC.
