27946-60-7

Usage

Uses

Used in Pharmaceutical Industry:
Methapyrilene is used as an antihistamine agent for treating allergic reactions and symptoms such as itching, sneezing, and watery eyes. Its H1 receptor antagonist activity helps in blocking the effects of histamine in the body, providing relief from these symptoms.
Used in Sleep Aid Formulations (Historic Use):
Methapyrilene was previously used as a sleep aid in some over-the-counter preparations due to its sedative and mild hypnotic effects. However, due to concerns over its side effects and potential for hepatic toxicity, its use in sleep aid formulations has been largely discontinued.

Upstream product

• 15184-99-3 N,N-dimethyl-3-methoxybenzylamine 
• 74-88-4 methyl iodide 

Downstream Products

• 36707-27-4 1,2-bis(3-methoxyphenyl)ethane 
• 1798-09-0 m-methoxyphenylacetic acid 

Relevant academic research and scientific papers

Ni-Catalyzed Iterative Alkyl Transfer from Nitrogen Enabled by the in Situ Methylation of Tertiary Amines

Current methods to achieve transition-metal-catalyzed alkyl carbon-nitrogen (C-N) bond cleavage require the preformation of ammonium, pyridinium, or sulfonamide derivatives from the corresponding alkyl amines. These activated substrates permit C-N bond cleavage, and their resultant intermediates can be intercepted to affect carbon-carbon bond-forming transforms. Here, we report the combination of in situ amine methylation and Ni-catalyzed benzalkyl C-N bond cleavage under reductive conditions. This method permits iterative alkyl group transfer from tertiary amines and demonstrates a deaminative strategy for the construction of Csp3-Csp3 bonds. We demonstrate PO(OMe)3 (trimethylphosphate) to be a Ni-compatible methylation reagent for the in situ conversion of trialkyl amines into tetraalkylammonium salts. Single, double, and triple benzalkyl group transfers can all be achieved from the appropriately substituted tertiary amines. Transformations developed herein proceed via recurring events: The in situ methylation of tertiary amines by PO(OMe)3, Ni-catalyzed C-N bond cleavage, and concurrent Csp3-Csp3 bond formation.