Ethyl 4-Hydroxypiperidine-1-Carboxylate: A Closer Look

Historical Development

Chemists started turning to piperidine structures in the late 19th century, tracing back to a period when medicinal chemistry began shifting focus from plant-derived compounds to synthetic molecules. French chemist L. Knorr, who dabbled in heterocyclic chemistry, explored piperidine rings early on, pivoting them into a cornerstone for pharmaceuticals. Ethyl 4-Hydroxypiperidine-1-Carboxylate gained traction as researchers realized the impact of functionalizing piperidine rings. In the 1980s, with spectrometry tools and better reaction controls, the path opened wider for synthesizing variations like this one, especially for medicinal use and as a building block in fine chemical manufacture.

Product Overview

Ethyl 4-Hydroxypiperidine-1-Carboxylate catches the interest of laboratory scientists and manufacturing engineers alike. It looks innocuous at first—usually a white or off-white crystalline powder—but it harbors a reactive mix of features. Market demand for this compound grows primarily from pharmaceuticals, agroscience, and, increasingly, high-end material science. Being a versatile intermediate, its functional groups enable synthesis of diverse molecules, including certain specialty drugs, crop protection compounds, and additives in polymer production.

Physical & Chemical Properties

This compound doesn’t give off much smell. Powder at room temperature, it melts at around 74–78°C and dissolves in common organic solvents, such as ethanol, chloroform, and a bit less in water. Molecular weight clocks in near 188 grams per mole. Its structure, featuring an ethyl ester and a hydroxy group at the fourth carbon of the piperidine ring, combines stability with useful reactivity: the hydroxy group opens doors for further reactions, whereas the ethyl ester withstands moderate reaction conditions.

Technical Specifications & Labeling

Chemical producers selling this compound keep purity high, often over 98% determined by HPLC. Typical containers are labeled with batch number, production date, storage instructions—usually keep cool and dry—and hazard statements in line with GHS regulations. Shipment follows guidelines for organic chemicals, with Material Safety Data Sheets (MSDS) required for large quantities. Regulatory compliance ensures traceability, crucial in pharmaceutical manufacturing.

Preparation Method

Synthesis relies on several steps: usually starting from piperidine, which undergoes hydroxy functionalization at the fourth position—by oxidation or direct substitution—before carboxylation at the nitrogen. Often, ethyl chloroformate serves as a carboxylating agent. What matters in scale-up is yield, purity, and minimization of byproducts. Reaction conditions, especially solvent choice and temperature, influence both efficiency and safety. Analytical QC checks run throughout, using NMR and LC-MS to confirm identity and spot impurities.

Chemical Reactions & Modifications

Few molecules offer the same options for modifications. The 4-hydroxy group allows alkylation, acylation, or even conversion to halides for further transformations. The ester group, in the presence of acid or base, gets hydrolyzed to give the free acid—another useful intermediate. Large-scale chemists take advantage of this reactivity to introduce various substituents, tailoring downstream compounds to suit specific drug profiles, crop science agents, or even new polymers.

Synonyms & Product Names

Chemical suppliers and regulatory bodies recognize it under several names. Some call it Ethyl 1-Carboethoxypiperidin-4-ol. Others use 4-Hydroxy-1-piperidinecarboxylic acid ethyl ester, sometimes short-handed as EHPCE or E4HPCE in specialty catalogs. Keeping track of these synonyms matters, especially in global procurement where regulatory forms and customs declarations switch between naming conventions.

Safety & Operational Standards

Like many organics, Ethyl 4-Hydroxypiperidine-1-Carboxylate requires gloves, goggles, and good ventilation in handling. Skin or eye contact may cause irritation. Spillage calls for rapid cleanup, since fine powder can get airborne. Storage in tightly closed containers, away from oxidizers and acids, cuts contamination risk. Labs and production plants enforce hands-on safety and routine air monitoring, pushing teams to respect handling procedures, not just file away compliance documentation.

Application Area

In pharmaceuticals, this compound ranks as a stepping stone toward active ingredients for CNS drugs, pain management compounds, and some antipsychotics. Agrochemical researchers lean on its flexible structure for crafting more selective and environmentally responsible pesticides. The physical chemists and material scientists borrow it to tweak polymer chains or create new surface-active agents. Its real impact shows across fields—if you follow patents, research articles, and regulatory submissions, demand crosses old boundaries, revealing new applications every year.

Research & Development

Every research chemist I’ve worked with wants tools that enable quick iteration. Ethyl 4-Hydroxypiperidine-1-Carboxylate fits because researchers can easily modify the molecule to probe different biological effects or physical properties. Many R&D projects today focus on designing CNS-active molecules where a 4-hydroxy-piperidine base provides the needed “scaffold”. Others explore the ring system for stability improvements, or lower toxicity than precursor chemicals. Academic labs and startups alike embrace it, feeding the compound into screens for bioactivity, optimizing side chains to tip the scales of selectivity or solubility.

Toxicity Research

Safety profiles drive every application. For Ethyl 4-Hydroxypiperidine-1-Carboxylate, animal studies reveal moderate acute toxicity—high doses trigger drowsiness, lowered motor function, and mild organ effects. Chronic studies remain rare, mainly because end products don’t always include this intermediate. Regulatory dossiers focus on mutagenicity and residual solvent levels, with raw material standards getting tighter every year. Responsible manufacturers commission third-party toxicity screening, a practice that helps everyone downstream: the closer to zero unknowns, the fewer surprises for both workers and patients.

Future Prospects

Synthetic chemistry evolves every decade, and intermediates like Ethyl 4-Hydroxypiperidine-1-Carboxylate stand right at the intersection of human health, food production, and new materials. Newer “green” synthesis methods—solvent-free, or using biocatalysts—hold promise for reducing environmental impact, scaling up production safely, and keeping costs reasonable. Drug designers will keep leveraging scaffolds like these as regulatory focus sharpens on molecular safety, not just efficacy. Data-sharing and global safety regulation set high standards, so every gram of intermediate entering the supply chain counts toward safer final products. Innovation in chemical routes and applications rests, in no small part, on keeping foundational compounds like this one available, affordable, and well-characterized.




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Ethyl 4-Hydroxypiperidine-1-Carboxylate
Ethyl 4-Hydroxypiperidine-1-Carboxylate
Ethyl 4-Hydroxypiperidine-1-Carboxylate