29122-69-8

Usage

Uses

Used in Pharmaceutical Industry:
2-[4-(2,3-EPOXYPROPOXY)PHENYL]ACETAMIDE is used as an impurity in the production of Atenolol, a medication prescribed for the treatment of various cardiovascular conditions such as hypertension, angina, and arrhythmias. Its presence in the manufacturing process is crucial for ensuring the quality and safety of the final product, as it helps in monitoring and controlling the purity of Atenolol.
Additionally, given its chemical structure and properties, there may be potential for further research and development in exploring its applications in other areas of the pharmaceutical industry, such as drug delivery systems or as a starting material for the synthesis of new compounds with potential therapeutic benefits. However, further investigation and validation would be required to confirm these possibilities.

InChI:InChI=1/C11H13NO3/c12-11(13)5-8-1-3-9(4-2-8)14-6-10-7-15-10/h1-4,10H,5-7H2,(H2,12,13)

Upstream product

• 106-89-8 epichlorohydrin 
• 623-05-2 (4-hydroxyphenyl)methanol 
• 17194-82-0 2-(4-hydroxyphenyl)acetamide 

Downstream Products

• 58027-20-6 2-{4-[3-(2-Benzenesulfonylamino-ethylamino)-2-hydroxy-propoxy]-phenyl}-acetamide 
• 115538-83-5 1--3-chloropropan-2-ol 
• 93379-54-5 (S)-Atenolol 
• 56715-13-0 (+)-(R)-atenolol 
• 29122-68-7 (RS)-atenolol 
• 79837-04-0 N-{3-[4-(2-amino-2-oxoethyl)phenoxy]-2-hydroxypropyl}-1H-benzimidazole-1-propanamine 
• 81346-72-7 (²H₆)-atenolol 
• 862422-88-6 2-[4-(3-benzylamino-2-hydroxy-propoxy)-phenyl]-acetamide 
• 33321-56-1 2-(4-{3-[2-(4-Acetylamino-phenoxy)-ethylamino]-2-hydroxy-propoxy}-phenyl)-acetamide 
• 81346-71-6 4-(3-amino-2-hydroxypropoxy)phenylacetamide 
• 143285-76-1 1-<2-(4-aminophenyl)-1,1-dimethylethylamino>-3-(4-carbamoylmethylphenoxy)propan-2-ol 

Relevant academic research and scientific papers

Solvent-Directed Epoxide Opening with Primary Amines for the Synthesis of β-Amino Alcohols

An efficient synthesis of β-amino alcohols from a variety of epoxides and primary unbranched amines in the absence of any catalyst in high yields and regioselectivities is reported. A variety of polar mixed solvent systems allow for the selective formation of secondary amino alcohols over tertiary amino alcohols. The reaction scope extends to a wide variety of aromatic and aliphatic substituted epoxides and primary amines bearing complex functionality.

Lipase-catalyzed green synthesis of enantiopure atenolol

A new green route is proposed for the synthesis of enantiopure atenolol (a β1-blocker). An enzymatic kinetic resolution approach was used to synthesize the enantiopure intermediates (R)- and (S)-2-(4-(3-chloro-2-hydroxypropoxy)phenyl)acetamide from the corresponding racemic alcohol. Of the commercially available lipases screened, Candida antarctica lipase-A (CLEA) showed maximum enantioselectivity in the transesterification of the racemic alcohol using vinyl acetate as the acyl donor. The reactions afforded the (S)-alcohol along with the (R)-acetate, with 48.9% conversion (E = 210, eeP = 96.9% and eeS = 91.1%). Various reaction parameters were optimized in order to achieve maximum enantioselectivity. N-alkylation of the (S)-alcohol with isopropylamine afforded the (S)-atenolol, and the (R)-acetate was chemically hydrolyzed to the corresponding alcohol and further converted to the (R)-atenolol via N-alkylation of the (R)-alcohol with isopropylamine. The use of ionic liquids, to solve the solubility related problems of the drug intermediates, made this process greener and more efficient compared to the previously reported methods. This journal is

Design, synthesis and evaluation of racemic 1-(4-hydroxyphenyl)-2-[3- (substituted phenoxy)-2-hydroxy-1-propyl]amino-1-propanol hydrochlorides as novel uterine relaxants

Novel 1-(4-hydroxyphenyl)-2-[3-(substituted phenoxy)-2-hydroxy-1-propyl] amino-1-propanol hydrochlorides were designed based on the pharmacophore for potent uterine relaxant activity and by utilizing the principles of structural hybridization. The designed molecules were synthesized as racemates by a novel route and were evaluated for uterine relaxant activity in vitro on isolated rat uterus and in vivo in pregnant rats. Their cAMP-releasing potential was studied using rat uterus tissue homogenates by the cAMP [3H] assay, and cardiac stimulant potential was evaluated on isolated guinea pig right atrium. All compounds exhibited potent uterine relaxant activity in vitro and produced a significant delay in the onset of labour in pregnant rats; their cAMP-releasing potential was slightly less, while their cardiac stimulant potential was insignificant as compared to isoxsuprine hydrochloride.

One pot synthesis of (±)/(S)-atenolol and (±)/(S)-propranolol by employing polymer supported reagent

(±)/(S)-Atenolol and (±)/(S)-propranolol were synthesized by using reaction of (±)/(S)-epichlorohydrin with polymer supported phenoxide anion followed by reaction with isopropylamine.

A synthesis of atenolol using a nitrile hydration catalyst

The synthesis of atenolol is described using a platinum containing homogeneous catalyst for the conversion of a nitrile to an amide. The catalytic reaction may be employed as the final step in the synthesis or in the preparation of the intermediate 4-hydroxyphenylacetamide. The structure of the nitrile intermediate, 1-(4′-cyanomethylphenoxy)-2-hydroxy-3-isopropylaminopropane, has been determined by X-ray crystallography.