This compound belongs to the class of organic compounds known as piperidines. These are compounds containing a piperidine ring, which is a saturated aliphatic six-member ring with one nitrogen atom and five carbon atoms.
External Descriptors
Not available
1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.
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Application Protocols
No application protocols (e.g., WB, IHC, IF, FC) apply to this chemical building block.
General handling suggestion for solution preparation (non-validated, literature/general):
To prepare a 0.1–1.0 M stock: dissolve the hydrochloride salt in water, MeOH, or DMSO. If the free base is required, add an equimolar to slight excess of base (e.g., DIPEA), extract into an organic solvent (EtOAc or CH2Cl2), dry, and use immediately or convert to a different salt for storage.
For reaction-specific procedures, refer to the Reaction Conditions tab. Always validate conditions at small scale and consult the SDS before use.
Biological Roles
No biological roles are specified for this catalog item. As a small organic building block, 3-ethoxypiperidine hydrochloride is intended for research and synthetic use only.
General/literature context:
Piperidine rings are “privileged” scaffolds in medicinal chemistry, frequently incorporated to modulate basicity, aqueous solubility, and receptor binding profiles in small molecules.
Ether substitution at the 3-position can influence conformational preferences of the piperidine chair and adjust physicochemical properties (e.g., reducing basicity relative to unsubstituted piperidine via inductive effects and adding lipophilicity via the ethoxy group).
The hydrochloride salt form is often selected in discovery chemistry to enhance handling and purity, rather than for any intrinsic biological function.
Important: This product is supplied for research use only (as per Product Data). It is not intended for use in humans or diagnostics and should not be described or used as having therapeutic or clinical activity.
Buffer Applications
This compound is not a conventional buffering agent and is not typically used to prepare defined pH buffer systems.
Practical guidance:
The hydrochloride salt dissolves readily in water, but pH will be acidic due to the protonated amine and chloride counterion. If used in aqueous reaction media, adjust pH with appropriate base (e.g., NaHCO3, Na2CO3, or organic bases) to access the free amine.
For biochemical buffers, select dedicated buffering systems (e.g., phosphate, HEPES, Tris) rather than amine building blocks.
Conclusion: No buffer recipes or pH ranges apply to this product; refer instead to the Reaction & Applications and Reaction Conditions tabs for relevant usage.
Green Alternatives
While the substance itself is a building block rather than a solvent, greener choices can be made for the media and methods used with it.
Greener solvent replacements (general guidance):
Replace chlorinated solvents (CH2Cl2, CHCl3) with 2-MeTHF, CPME, or EtOAc for acylations and extractions after neutralizing to the free base.
Use MeCN or EtOAc instead of DMF/DMSO when feasible to ease workup; or apply propylene carbonate for polar aprotic needs when elevated temperatures are acceptable.
Comparison (general):
CH2Cl2 vs 2-MeTHF: similar medium polarity for amide couplings; 2-MeTHF is biorenewable, less hazardous, and has a higher boiling point facilitating recovery.
DMF vs MeCN/EtOAc: MeCN/EtOAc lower environmental persistence and easier removal; coupling efficiency may require reagent tuning.
Process intensification:
Utilize solvent-minimized protocols (neat or high-solids couplings) when possible.
Consider aqueous micellar catalysis for certain N-acylations or reductive aminations (surfactant-enabled), keeping in mind the salt’s high aqueous solubility.
Waste and workup:
Generate HCl neutralization salts stoichiometrically; plan for brine minimization and chloride-containing aqueous waste handling.
Employ in-line base scavengers or solid-supported reagents to reduce solvent volumes and salt waste.
Note: These are general/literature recommendations intended to support greener workflow choices; validate at lab scale before scale-up.
Pharmaceutical Uses
No pharmacopeial status, excipient role, or formulation specifications are provided for this item.
General/literature context (non-clinical):
3-Ethoxypiperidine motifs may serve as intermediates in the synthesis of drug candidates where saturated nitrogen heterocycles are required to tune physicochemical properties.
The hydrochloride salt is commonly chosen for intermediates to improve crystallinity, ease of handling, and assay accuracy during API intermediate manufacture.
If used in a GMP environment, users should qualify the material per their quality system, including identification, assay, residual solvents, and elemental impurities as required by ICH guidelines.
Important restriction: For research use only (per Product Data). No therapeutic or clinical claims are made or implied for this catalog product.
Physical Properties
Item-specific physical constants are not provided for this SKU.
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Molecular weight (computed, literature for HCl salt of 3-ethoxypiperidine): ~165.66 g/mol (C7H16ClNO). Label as literature/computed; not an item specification.
Molecular formula (literature, free base vs. salt): free base C7H15NO; hydrochloride C7H16ClNO. Label as literature; not an item specification.
Physical state: Typically an organic amine hydrochloride salt is a crystalline solid (literature/general). Not item-specific.
Solubility (literature/general): amine hydrochlorides are usually highly soluble in water and polar protic solvents (e.g., MeOH, EtOH); moderate in DMSO/DMF; sparing in nonpolars. Actual solubility for this item: Not specified; verify experimentally.
Melting point, boiling point, density, refractive index, pKa, logP: Not specified for this item; refer to CoA/Spec Sheet.
Notes for practitioners (general guidance):
If preparing stock solutions, start with water, MeOH, or EtOH; adjust pH to liberate free base if needed for solubility in organic media. Confirm identity and purity by NMR/LC–MS before process use.
For chromatographic handling, convert to free base to improve retention in normal-phase systems or maintain as HCl salt for aqueous HPLC.
Quality & Grades
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
Guidance on interpreting grades (general):
Research-grade organic building blocks are typically supplied at assay levels suitable for synthesis. If you require specific trace impurity limits (e.g., residual solvents, metals) or spectral purity criteria, request the CoA/Spec Sheet for this lot.
For chromatography-sensitive applications, low-UV absorbing impurities and amine-related background can be important; consider HPLC assay and UV scan data if available.
Stabilizers: None specified for this item; refer to CoA/Spec Sheet. Amine hydrochlorides generally do not require added stabilizers and are often preferred for bench stability and handling.
Batch-specific documentation: Aladdin provides CoA with assay, identity (NMR/IR/LC–MS), and, when applicable, water content (Karl Fischer) and residual solvent data. If these are critical for your process qualification, request the current lot’s documentation prior to use.
Practical notes for this scaffold:
The HCl salt form is typically chosen to enhance crystallinity, reduce volatility/odor, and improve weighing accuracy versus the free base—useful for parallel synthesis workflows.
If a base-free environment is required (e.g., for acid-catalyzed steps), ensure residual inorganic chloride and acidity are compatible with your process or convert to the free base before use.
Reaction & Applications
3-Ethoxypiperidine hydrochloride is a versatile saturated nitrogen heterocycle building block. The protonated salt is ideal for storage/handling; the free base (generated in situ or pre-formed) is the reactive intermediate.
N-Acylation and carbamate formation: rapid amide formation with acid chlorides or via coupling reagents (EDC/HOBt, HATU, T3P) to furnish amide libraries featuring a 3-ethoxypiperidinyl motif.
Sulfonamide/urea/sulfonylurea synthesis: reaction with sulfonyl chlorides or with CDI/carbonyldiimidazole-activated carbonyls to afford ureas/carbamates.
N-Alkylation: SN2 alkylation under basic conditions (e.g., K2CO3/MeCN) using alkyl halides; for cleaner profiles, reductive amination with aldehydes/ketones (NaBH3CN, NaBH(OAc)3) is often preferred.
Salt/base toggling: in situ neutralization (DIPEA, Et3N, or inorganic base) liberates the nucleophilic amine for coupling without isolation of the free base.
Scaffold use in medicinal chemistry: the 3-alkoxy piperidine ring is a common motif to tune basicity, polarity, and solubility; the ethoxy substituent provides increased lipophilicity and conformational bias compared with unsubstituted piperidine.
Practical tips:
Start with 2–3 equiv of organic base in amide couplings to compensate for HCl and ensure full amine availability.
For sensitive electrophiles, pre-form the free base by basification and extraction to avoid localized acid effects.
Employ non-nucleophilic bases (DIPEA) to minimize side reactions; consider buffered conditions in reductive aminations to control iminium formation.
Reaction Conditions
General, literature-based guidance for typical transformations with 3-ethoxypiperidine (applies after neutralizing the HCl salt):
Amide couplings:
Solvents: DMF, MeCN, DCM, or greener 2-MeTHF/EtOAc.
Reagents: HATU/DIPEA (rt to 40 °C, 1–4 h), EDC·HCl/HOBt or Oxyma/DIPEA (rt to 40 °C, 2–12 h), T3P/Et3N (rt, 1–3 h).
Notes: use 2–3 equiv base to neutralize HCl and activate amine. Monitor by LC–MS.
Sulfonamide formation:
Solvent: DCM or MeCN.
Base: DIPEA or NaHCO3 (aq biphasic).
Temp: 0 °C to rt; 0.9–1.1 equiv sulfonyl chloride; 1–3 h.
Reductive amination (N-alkylation):
Solvent: MeOH, EtOH, or MeCN.
Conditions: carbonyl (1.1–1.5 equiv), AcOH (0.5–1 equiv) to form iminium; reduce with NaBH3CN (rt, 2–6 h) or NaBH(OAc)3 (rt, 4–16 h). Quench, basify, extract.
N-Alkylation via SN2:
Solvent: MeCN, acetone.
Base: K2CO3 or Cs2CO3, 1.5–3 equiv; alkyl bromide/iodide 1.1–1.5 equiv; 40–60 °C, 4–24 h.
Workup considerations:
Where needed, convert products to HCl salts by HCl in dioxane or isopropanol to aid isolation.
Beware emulsions with chloride-rich aqueous layers; brine and phase separators help.
All parameters are literature/general guidance and should be optimized for the specific substrate set; no item-specific performance claims are made.
Safety & Handling
Hazard classification is not provided in the product data. Always consult the product SDS for authoritative safety information.
GHS classification, signal word, H-statements, pictograms: Not specified for this item; refer to SDS.
General hazards (literature/general for amine hydrochloride salts): may cause irritation to skin, eyes, and respiratory tract. Dust may be irritating. Avoid inhalation and contact.
Recommended PPE: lab coat, safety glasses or goggles, appropriate chemical-resistant gloves (e.g., nitrile), and use in a fume hood when handling powders or preparing solutions.
Incompatibilities (general): strong bases (will liberate the free base), strong oxidizers. Avoid mixing with bases in confined vessels due to potential heat evolution upon neutralization.
Peroxide formation: not applicable to this salt; no known peroxide-forming tendency (general note).
First-aid overview (general):
Inhalation: move to fresh air; seek medical advice if symptoms persist.
Skin contact: wash with soap and water; remove contaminated clothing.
Eye contact: rinse cautiously with water for several minutes; remove contact lenses if present and easy to do; continue rinsing.
Ingestion: rinse mouth; do not induce vomiting; seek medical attention.
Spill response: avoid dust generation; sweep up with minimal dispersion; dispose of in accordance with local regulations.
Fire safety: use CO2, dry chemical, or foam. Combustion may release HCl and nitrogen oxides; firefighters should wear self-contained breathing apparatus.
Storage conditions per Product Data: Room temperature. Shipped: Normal. Keep tightly closed, dry, and away from strong bases and oxidizers.
Solvent Selection
This product is an amine hydrochloride salt; solvent choice depends on whether you use it as the salt or convert to the free base.
Polarity/miscibility (literature/general):
As HCl salt: high solubility expected in water and polar protic solvents (MeOH, EtOH); good in DMF/DMSO; limited in nonpolar solvents.
As free base: increased solubility in moderately polar organics (EtOAc, CH2Cl2, MeCN, 2-MeTHF); reduced in water at neutral/basic pH.
Typical use scenarios:
Amide/sulfonamide formation: dissolve salt in DMF/MeCN with organic base (DIPEA, Et3N) to liberate free amine in situ.
N-alkylation/reductive amination: pre-neutralize with base, extract free base into an organic solvent (e.g., CH2Cl2, EtOAc), or conduct in alcohols with base present.
Aqueous-phase transformations: salt form is advantageous for phase-transfer or biocatalytic steps if pH is controlled.
Quick comparison (general):
Water/MeOH: best for initial dissolution of salt; may require basification to access nucleophilic free amine.
MeCN/DMF/DMSO: good for coupling chemistry; watch for downstream removal.
2-MeTHF/EtOAc: greener options post-neutralization; suitable for extractions and many acylations.
Tips:
If crystallization of intermediates is desired, consider free-base extraction to tune solubility/partitioning.
Monitor pH; nucleophilicity is suppressed in the protonated state—ensure sufficient base equivalents in situ.
Storage & Reconstitution
Storage conditions (from Product Data): Room temperature. Store tightly closed in a dry place. Protect from strong bases and oxidizers. Shipped under normal conditions.
Stability (general): amine hydrochloride salts are typically stable at ambient conditions. Avoid prolonged exposure to moisture to prevent caking or deliquescence (general guidance; not an item specification).
Reconstitution/preparation (general guidance):
Aqueous solutions: dissolve the required amount in deionized water. The pH will be acidic; adjust as needed for your application.
Organic solutions: if the free base is needed, neutralize a portion of the solid with base (e.g., DIPEA or NaHCO3) and extract into an organic solvent (EtOAc, CH2Cl2, 2-MeTHF). Use immediately to minimize amine oxidation.
Filtration/sterilization: if a sterile solution is required for certain workflows, filter through a 0.22 µm membrane; avoid heat sterilization unless stability is confirmed.
Freeze–thaw: not typically applicable since the material is supplied as a solid; if solutions are prepared, store aliquots to minimize freeze–thaw cycles. For DMSO or aqueous stocks, common practice is −20 °C storage; verify solubility and stability empirically.
Documentation: For lot-specific details (assay, water content, residual solvents), consult the CoA/Spec Sheet. Research use only.
Structure & Identity
3-Ethoxypiperidine hydrochloride is a saturated six-membered nitrogen heterocycle (piperidine) bearing an ethoxy substituent at the 3-position, isolated as the amine hydrochloride salt.
SKU: E347267
Product name: 3-Ethoxypiperidine hydrochloride
CAS: 1159826-79-5
PubChem CID: 45075370
InChIKey: 70625 (as provided; note: this appears non-standard/truncated—verify against CoA/SDS)
SMILES: Not specified for this item; refer to CoA/Spec Sheet.
Molecular formula: Not specified for this item; refer to CoA/Spec Sheet.
Molecular weight: Not specified for this item; refer to CoA/Spec Sheet.
Structural features (general/literature description):
Core ring: piperidine (saturated C5–N ring) with a protonatable secondary amine at nitrogen, present here as the ammonium chloride salt.
Substituent: an alkoxy group (–OCH2CH3) at the 3-position of the ring, making the molecule a 3-alkoxy piperidine scaffold.
Ionic form: as the HCl salt, the nitrogen is quaternized to the ammonium chloride, improving crystallinity and aqueous solubility compared with the free base.
Stereochemistry: none specified; the 3-substituted piperidine center can be prochiral/chiral depending on substitution pattern, but no defined stereochemistry is indicated for this product.
2D description in words:
A six-membered ring containing one nitrogen (position 1). At ring carbon 3, an oxygen substituent extends to an ethyl group (–O–CH2–CH3). The nitrogen is protonated with a chloride counterion in the isolated salt.
Synthetic Utility
Functional elements and reactivity (literature/general):
Secondary amine (as HCl salt): upon neutralization, serves as a potent nucleophile for acylation, sulfonylation, carbamoylation, and reductive amination, enabling rapid diversification at nitrogen.
3-Ethoxy substituent: an inert aliphatic ether under most conditions; generally stable to bases and many nucleophiles. It modulates sterics/electronics of the ring but is not typically a reactive handle without strong conditions.
Key transformations:
Amide formation with acid chlorides/anhydrides or coupling reagents (EDC/HATU/T3P). Suitable for parallel library synthesis.
Urea/carbamate formation via CDI or chloroformates.
Sulfonamide introduction with sulfonyl chlorides (base-mediated).
N-alkylation via SN2 (alkyl halides, Mitsunobu-activated alcohols) or reductive amination (NaBH(OAc)3, NaBH3CN).
Salt/base management: in situ liberation using DIPEA or Et3N (2–3 equiv) to overcome protonation and generate the free amine.
Retrosynthetic value:
The 3-alkoxy piperidine core can be embedded into targets requiring basic, conformationally restricted amine centers. The ethoxy group can be exchanged only under harsh dealkylation (e.g., strong Lewis acids) and is generally considered a stability element rather than a handle.
Selectivity/practical tips:
Use non-nucleophilic bases to minimize N→O acyl transfer or ether cleavage side reactions.
If downstream salt formation is desired (e.g., for isolation), convert coupled products to their hydrochloride or mesylate salts for improved crystallinity.
Target Specificity
Not applicable. This product is a small-molecule building block and not a biological targeting reagent. No antigen, epitope, clone, isotype, or species reactivity information applies.
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