132906-03-7

Usage

Type of compound

Ester derivative

Components

1-Piperidinecarboxylic acid and 4-methoxyphenol

Usage

Pharmaceutical production, research

Pharmacological properties

Potential as a psychiatric drug, antitumor and anti-inflammatory activities

Chemical structure

Promising candidate for drug development

Further research

Necessary to understand potential uses and applications in medicine and pharmacology.

Upstream product

• 110-89-4 piperidine 
• 50780-53-5 Carbonic acid chloromethyl ester 4-methoxy-phenyl ester 
• 7693-41-6 4-methoxyphenylchloroformate 
• 150-76-5 4-methoxy-phenol 

Relevant academic research and scientific papers

Preparation of Carbamates, Esters, Amides, and Unsymmetrical Ureas via Br?nsted Acid-Activated N-Acyl Imidazoliums

We report the application of Br?nsted acid-activated N-acyl imidazoliums as versatile intermediates in carbonyl transformations. The efficient and scalable procedure was validated on a diverse set of carbamates, esters, amides, and unsymmetrical ureas (21 examples, up to 91% yield). Additionally, we exemplify this method on multikilogram scale for the synthesis of an electron-deficient carbamate.

Structure-reactivity correlations in the aminolysis of aryl chloroformates

The reactions of a series of secondary alicyclic amines with 4-methylphenyl and 4-methoxyphenyl chloroformates are subjected to a kinetic investigation in water, at 25.0°C, ionic strength 0.2 M (KCI). Under amine excess, pseudo-first-order rate coefficients (kobs) are found for all reactions. Plots of kobs vs [NH] (NH is the free amine) are linear, with the slope (kN) pH independent, except the reactions of l-(2-hydroxyethyl)piperazine with both substrates at pH 6.2-7.3. The Broensted-type plots for the kN values for the aminolysis of both chloroformates are linear, with slopes ca. 0.3, which is consistent with rate-determining formation of a zwitterionic tetrahedral intermediate (T±). With the PKa and log kN data for the present reactions, together with those for the same aminolysis of phenyl and 4-nitrophenyl chloroformates, two dual parametric equations are found for log kN as a function of pKa of the nucleophile, Hammett sigma of the "nonleaving" group, and pKa of the "nonleaving" group, with coefficients βN = 0.3, ρnlg = 0.7, and βnlg = -0.2, respectively.

α-Haloalkyl Haloformates and Related Compounds 1. A Convenient Synthesis of Carbamates via Chloromethyl Carbamates

The preparation of carbamates under mild conditions utilizing a new class of activated carbonates (containing chloromethyl function) is described.