An efficient synthesis of 2-(4-(benzyloxy)phenyl)-N, N-dimethylacetamide substantially free from impurities – Synthesis & characterization of novel impurities

[Display omitted] •Alkylation of phenol over phenylacetamides using phase transfer catalyst.•Direct preparation of hydroxy phenyl acetamide without protection.•Synthesis of O-desmethylvenlafaxine intermediate controlling process impurities.•Novel impurities were identified, synthesized and character...

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Bibliographic Details
Published in:Results in Chemistry 2021-01, Vol.3, p.100160, Article 100160
Main Authors: Sonavane, Sachin, Mokal, Sachin, Wadekar, Shubham, Wakchaure, Satish, Deshmukh, Sharayu
Format: Article
Language:English
Subjects:
Analysis
Desvanlafaxin
Impurities
Process
Synthesis
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Summary:[Display omitted] •Alkylation of phenol over phenylacetamides using phase transfer catalyst.•Direct preparation of hydroxy phenyl acetamide without protection.•Synthesis of O-desmethylvenlafaxine intermediate controlling process impurities.•Novel impurities were identified, synthesized and characterized. An improved process developed for the 2-(4-(Benzyloxy)phenyl)-N, N-dimethylacetamide (BPA) which is key starting material for the synthesis of drug O-desmethylvenlafaxine succinate and asperphenamate was described to eliminate the impurities which will be formed during the process. The best reaction conditions were identified by evaluating the impurity profile and their formation during the synthesis. The optimization of the process was made to control the impurities which was one of the critical parameters in the synthesis of BPA. Both the novel impurities formed during the synthesis were identified, synthesized and characterized.
ISSN:2211-7156
2211-7156
DOI:10.1016/j.rechem.2021.100160