This compound belongs to the class of organic compounds known as piperidinecarboxamides. These are compounds containing a piperidine ring substituted with a carboxamide functional group.
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.
Certificati (CoA, COO, BSE/TSE e tabella di analisi)
C of A & Other Certificates(BSE/TSE, COO):
Analytical Chart:
Proprietà chimiche e fisiche
Peso molecolare
144.170 g/mol
XLogP3
-1.000
Hydrogen Bond Donor Count
2
Hydrogen Bond Acceptor Count
2
Rotatable Bond Count
0
Exact Mass
144.09 Da
Monoisotopic Mass
144.09 Da
Topological Polar Surface Area
66.600 Ų
Heavy Atom Count
10
Formal Charge
0
Complexity
130.000
Isotope Atom Count
0
Defined Atom Stereocenter Count
0
Undefined Atom Stereocenter Count
0
Defined Bond Stereocenter Count
0
Undefined Bond Stereocenter Count
0
The total count of all stereochemical bonds
0
Covalently-Bonded Unit Count
1
Calcolatori di soluzioni
Molarity Calculator
Determine the necessary mass, volume, or concentration for preparing a solution.
Dilution Calculator
Determine the dilution needed to prepare a stock solution.
Reconstitution Calculator
Recensioni
Recensioni dei clienti
Application Protocols
Not applicable. No validated bioassay protocols (e.g., WB, IHC, IF, FC) are associated with this small‑molecule reagent. For use in chemical synthesis or screening, follow the Reaction Conditions and Synthetic Utility sections above, and consult primary literature for procedure details tailored to your transformation.
Biological Roles
This section provides general chemical‑biology context only; no medical/clinical claims.
Chemical features relevant to biology: The scaffold presents multiple hydrogen‑bond donors/acceptors (urea –NH/CO and an –OH), often desirable in ligand design for polar binding sites (kinases, proteases, transporters). The urea motif mimics peptide backbones and can serve as a bidentate H‑bonding element; the 4‑substituted piperidine ring is a common pharmacophore in probe molecules.
Permeability/solubility implications (literature): Urea plus alcohol functionality typically lowers lipophilicity and can reduce passive membrane permeability while improving aqueous solubility—useful for enzyme or transporter‑facing chemotypes or as a polar handle for prodrug/linker elaboration.
Metabolic considerations (general): Potential biotransformations include Phase I oxidation at C4 (if not protected), and Phase II conjugation (glucuronidation/sulfation) of the alcohol and possibly N‑acylation/deacylation dynamics of the urea under enzymatic conditions. The ring nitrogen is acylated and thus not protonated under physiological pH, reducing basicity‑driven tissue accumulation relative to tertiary piperidines.
Use in chemical biology workflows: Frequently employed as a fragment or intermediate to introduce a piperidinyl‑urea vector into screening libraries, covalent‑warhead linkers (after conversion to isocyanates/carbamates), or solubilizing appendages.
Note: Item‑specific biological data are not provided for this product; verify suitability in your assay system.
Buffer Applications
Not typically applicable. 4‑Hydroxypiperidine‑1‑carboxamide is not a conventional buffering agent. The ring nitrogen is acylated (urea), rendering it weakly basic; the molecule lacks a conjugate acid/base pair in a biologically useful range. For preparation and handling in aqueous systems, choose an external buffer (e.g., phosphate, HEPES) appropriate to your application.
If you must dissolve this compound for bioassays, typical vehicles include water, PBS, or mixtures with DMSO; adjust pH using a compatible buffer system rather than relying on the compound itself.
Green Alternatives
Context: This compound is a solid building block rather than a process solvent; “green” considerations focus on choice of reagents/solvents for its transformations and on isolation strategies.
Greener choices for common steps (literature guidance)
Alcohol activation/substitution:
Prefer sulfonate formation with p‑toluenesulfonic anhydride (Ts2O) or MsCl in greener solvents (ethyl acetate, 2‑MeTHF) with DBU/DIPEA, avoiding halogenated media.
For SN2, consider water/EtOH with phase‑transfer catalysts where feasible to reduce dipolar aprotic usage.
Oxidation to ketone:
Select catalytic TEMPO/bleach (pH‑controlled aqueous biphasic) or aerobic Cu/TEMPO systems in MeCN/H2O instead of Swern or Dess–Martin to minimize waste and hazards.
Urea N‑functionalization:
Use coupling agents with improved EHS profiles (e.g., CDI, DSC) rather than acid chlorides when possible; run in green(er) solvents like MeTHF, CPME, EtOAc.
Small comparison (qualitative)
Swern/DMP vs TEMPO/bleach: Swern/DMP give excellent yields but generate halogenated or hypervalent iodine waste; TEMPO/bleach is aqueous, inexpensive, and scalable with proper containment.
DMF/DMSO vs 2‑MeTHF/EtOAc: Polar aprotics maximize solubility but are less green; MeTHF/EtOAc improve EHS but may require co‑solvents or higher temperatures.
Operational tips
Favor crystallization from alcohols/EtOAc over chromatography where possible.
Implement solvent recovery for DMSO/DMF runs; consider water‑lean workups to reduce aqueous waste.
Pharmaceutical Uses
No excipient or pharmacopeial role is specified for this item; refer to CoA/Spec Sheet for any regulatory details.
General formulation/manufacturing context (non‑clinical)
Role as an intermediate: The 4‑hydroxy piperidinyl‑urea motif is a common intermediate in the synthesis of research compounds and candidate drug substances. It can be elaborated into carbamates, ethers, or ketones at C4, and further diversified on the urea nitrogen.
Salt formation: Because the ring nitrogen is acylated, classical amine salt formation is disfavored; formulation typically uses the neutral free base. Solubilization relies on co‑solvents (water/alcohols) or formation of hydrogen‑bonded solvates/co‑crystals.
Solid‑form considerations: Urea functional groups can engender rich hydrogen‑bond networks, potentially leading to polymorphism. For scale‑up, screen crystallization solvents to secure a stable form with acceptable handling properties (flowability, hygroscopicity). No item‑specific polymorph data are provided.
All uses are for research and development only. No therapeutic claims are made or implied.
Physical Properties
Item-specific (from Product Data)
Appearance: 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.
Literature/general properties (non-specification)
Physical state: typically a polar solid due to one urea carbonyl, one –NH2, and one –OH (literature expectation for this scaffold).
Acid/base: ring nitrogen is acylated (urea), thus significantly deactivated as a base; the molecule behaves as a neutral, highly hydrogen‑bonding species. The terminal urea –NH2 and the alcohol –OH can donate H‑bonds; the carbonyl and ring nitrogen can accept.
Solubility profile (qualitative, literature): expected good solubility in polar protic and aprotic media (water, methanol, ethanol, DMSO, DMF) due to multiple heteroatoms; poor solubility in nonpolar solvents (hexanes, toluene).
Partitioning: low to moderate hydrophilicity (cLogP likely low; no item‑specific value provided).
Thermal behavior: urea derivatives often melt/decompose rather than distill; drying under high vacuum at mild temperature is commonly feasible for analogous compounds.
If precise values (mp, bp, density, refractive index, pKa, logP, water content, residual solvents) are required for your lot, please consult the item’s CoA/Spec Sheet.
Quality and Grades
Item-specific (from Product Data)
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
Stabilizers/Inhibitors: Not specified for this item; refer to CoA/Spec Sheet.
Guidance on interpreting grades (general)
Research grade: Suitable for most discovery chemistry, screening, and synthesis. Typical controls include identity (NMR/HRMS/IR), purity by HPLC/GC, and water/byproducts limits. If you require trace‑metal specifications or residual solvent profiles, request the current CoA.
HPLC/LC–MS suitability: For heteroatom‑rich, polar solids like urea‑functionalized piperidines, low UV background and clean chromatograms are important in analytical workflows. If HPLC grade is needed (e.g., for reference standards), specify this at ordering; otherwise, typical research grade is adequate for synthesis and SAR work.
Stabilizer implications: This class does not typically require stabilizers; however, moisture content can influence handling, crystallinity, and assay. If Karl Fischer or headspace GC data are critical for your application, obtain lot‑specific data.
Recommendations
Verify acceptance criteria relevant to your use case (purity threshold, residual solvent panel, water content, and salt/ash) on the lot CoA.
For bioassay or screening, you may prefer lots qualified by NMR (>95% by 1H NMR) and LC (>95% area); for scale‑up, confirm impurity profile and polymorph if applicable.
Reaction and Applications
Focus: 4‑Hydroxypiperidine‑1‑carboxamide is a bifunctional building block combining a secondary alcohol (at C4) with an N‑substituted urea motif. It is useful in heterocycle elaboration, medicinal chemistry, and linker/scaffold synthesis.
Representative application families (literature)
C4 functionalization via activation of the alcohol: convert the secondary –OH to a sulfonate ester (MsCl/TsCl, base), then perform SN2 substitution with N/O/S nucleophiles to access 4‑substituted piperidine ureas. For less nucleophilic partners, halogenation (e.g., SOCl2 with DMF cat.; PPh3/CBr4) gives 4‑chloro/bromo derivatives.
Oxidation: secondary alcohol → ketone (4‑piperidone‑1‑carboxamide) using TEMPO/bleach, Swern, Dess–Martin, or catalytic Ru/AcOOH. The ketone opens routes to reductive amination libraries (diverse amines at C4).
Urea derivatization: the terminal –NH2 on the carbamoyl can be acylated/sulfonylated or converted to N‑alkyl/aryl ureas. Reaction with electrophiles (acyl chlorides, sulfonyl chlorides, isocyanates) forms N‑substituted ureas/imides.
Dehydration to isocyanate (advanced): primary ureas can be dehydrated to isocyanates (e.g., with POCl3/Et3N or CDI variants), enabling subsequent Curtius‑like insertion chemistry; conditions require careful optimization to avoid ring functional group scramble.
Protection strategies: protect –OH as TBS/TBDPS or carbonate to enable selective urea derivatization; alternatively, protect the urea –NH2 (e.g., Boc on the terminal nitrogen) to direct C4 chemistry.
Practical tips
Maintain anhydrous conditions for sulfonylation/halogenation steps. Urea functionality can hydrogen bond strongly—use polar aprotic media to maintain solubility.
For SN2 at C4, consider neighboring‑group effects and ring conformation; warming (40–80 °C) and high‑boiling polar solvents often improve conversions.
Reaction Conditions
General guidance from literature (non‑specification; optimize per substrate)
Alcohol activation to mesylate/tosylate: MsCl or TsCl (1.2–1.5 equiv), base (Et3N, DIPEA, or pyridine, 2–3 equiv), solvent CH2Cl2, EtOAc, or DMF, 0 °C → rt, 1–3 h. Workup with aqueous bicarbonate; isolate by precipitation or extraction. For greener media, use EtOAc/2‑MeTHF.
SN2 substitution at C4: Nucleophile (2–5 equiv), polar aprotic solvent (DMF, DMSO, MeCN), 40–90 °C, 2–18 h. For halides as leaving group, add iodide (NaI) as Finkelstein promoter when needed.
Oxidation to ketone: TEMPO (1–5 mol%), NaOCl (household bleach adjusted to pH ~9), KBr (co‑cat.), solvent MeCN/H2O 1:1, 0–25 °C, 1–4 h. Alternatively, Dess–Martin (1.3 equiv) in CH2Cl2 at 0 °C → rt, 1–2 h.
Reductive amination of 4‑ketone: amine (1.2–2.0 equiv), AcOH or TFA (cat.), solvent MeOH/EtOH/IPA, NaBH3CN or NaBH(OAc)3, 0–25 °C, 2–16 h. Hydrogenation option: H2 (1–5 bar), Pd/C (5–10 wt%), alcohol solvent, rt–50 °C.
Urea N‑acylation/sulfonylation: acyl/sulfonyl chloride (1.1–1.5 equiv), base (Et3N, NMM), solvent CH2Cl2/DMF, 0 °C → rt, 1–6 h. Monitor for over‑acylation.
Dehydration to isocyanate (advanced): POCl3 (2–3 equiv), base (Et3N), solvent toluene/CH2Cl2, 0 °C → 60 °C; conduct under anhydrous conditions and trap in situ with alcohol/amine.
Notes
Strong hydrogen bonding can slow extractions; salt out with brine and use polar organic layers (n‑BuOAc/EtOAc) to improve phase separation.
For scale‑up, prefer crystallization‑induced purifications from alcohol/EtOAc mixtures to minimize silica waste.
Safety and Handling
Item-specific (from Product Data)
GHS classification: Not specified for this item; refer to SDS.
Signal word / H‑Statements / Pictograms: Not specified for this item; refer to SDS.
Storage conditions: Room temperature (per Product Data).
General safety guidance (literature and best practice; defer to SDS for authority)
Expected hazards: Urea‑ and amino‑alcohol–containing heterocycles are often of low to moderate acute toxicity but can cause irritation to skin, eyes, and respiratory tract. Avoid dust formation and inhalation. Handle in a fume hood.
PPE: lab coat, safety glasses or splash goggles, and appropriate chemically resistant gloves (e.g., nitrile). Consider double‑gloving for extended handling.
Incompatibilities: Strong oxidizers and strong acids/bases may cause degradation (hydrolysis of urea, dehydration/oxidation of the alcohol). Avoid isocyanate‑forming dehydrating agents unless intended.
First aid (overview): In case of contact, rinse skin/eyes with water for at least 15 minutes. If inhaled, move to fresh air. If ingested, rinse mouth; do not induce vomiting; seek medical attention. Provide SDS to responders.
Spill/cleanup: Collect solids by gentle sweeping or HEPA vacuum; minimize dust. Wash residue with water/soap, or a compatible polar solvent if appropriate. Dispose of waste per institutional and local regulations.
Fire: Use water spray, CO2, dry chemical, or foam. Combustion may produce NOx and CO/CO2.
Solvent Selection
Applicability
This product is a polar, hydrogen‑bonding heterocycle (urea + alcohol). Solvent choice is driven by solubility and downstream transformation (e.g., protection, oxidation, substitution at C4).
General miscibility and polarity (literature; qualitative)
DMSO/DMF: maximize solubility for coupling, sulfonylation (to make mesylate/tosylate), or SN2 substitutions at C4 after activation.
Alcoholic solvents (MeOH/EtOH): convenient for crystallization/recrystallization and for catalytic oxidations of secondary alcohols; also useful as benign media in biocatalytic steps.
Water or aqueous mixtures: facilitate enzymatic transformations, carbonate/bicarbonate‑buffered acylations, and green oxidations.
EtOAc/MeCN: suitable for extractions and medium‑polarity chromatographic elution; often used in workups of urea‑containing compounds.
Comparison (qualitative)
DMSO vs DMF: DMSO offers higher polarity and better solubilization but is harder to remove; DMF is easier to strip and compatible with many coupling reagents.
MeOH vs i‑PrOH: MeOH dissolves more but can participate in transesterification; i‑PrOH is less reactive and greener for some steps.
Storage and Reconstitution
Item-specific (from Product Data)
Storage conditions: Room temperature.
Shipped in: Not specified for this item; refer to CoA/Spec Sheet.
General guidance (non‑specification)
Container: Store tightly closed in a clean, dry, inert container. A desiccator or dry‑box storage is recommended to maintain consistent assay and handling, as urea/alcohol functionalities can engage moisture.
Light/air: Normal laboratory lighting is acceptable; minimize prolonged exposure to high humidity. Inert gas blanket is optional for long‑term storage.
Reconstitution/dissolution: For stock solutions, use high‑purity water, methanol, ethanol, or DMSO depending on application. Typical screening stocks are 10–100 mM in DMSO; filter (0.2 µm PTFE) if needed. Label with concentration, solvent, and date.
Solution stability: Polar urea/alcohol solutions are generally stable for days to weeks at 2–8 °C; for long‑term, aliquot and freeze (–20 °C) to avoid repeated freeze–thaw. Verify stability by LC/MS before critical experiments.
Disposal: Dispose of solids/solutions according to institutional chemical waste protocols; avoid drain disposal unless permitted by local regulations.
Research use only: Per Product Data, this material is for research use only; not for human or veterinary use.
InChIKey: Not specified for this item; refer to CoA/Spec Sheet.
SMILES: Not specified for this item; refer to CoA/Spec Sheet.
Literature/Computed identifiers and structural description (non-specification)
Common structural class: substituted piperidine (six‑membered saturated heterocycle) bearing a urea (carbamoyl) substituent on the ring nitrogen and a secondary alcohol at C4.
2D structure in words: A chair‑like piperidine ring with the ring nitrogen N1 bearing a carbamoyl group (–C(=O)–NH2). At the 4‑position of the ring (para to the nitrogen in a six‑membered saturated system) resides a hydroxyl substituent (–OH) on a secondary carbon. The urea carbonyl provides one H‑bond acceptor; the terminal –NH2 and the –OH are H‑bond donors. No stereocenters are mandated unless the 4‑OH is specified as axial/equatorial in conformers; overall achiral as drawn.
Notes
All formula/MW/SMILES above are provided as general literature descriptors of the named structure and are not item‑specific specifications.
Synthetic Utility
Functional group synopsis
Urea (–NH–C(=O)–N–): bifunctional H‑bonding unit, nucleophilic at the terminal –NH2, electrophilic at the carbonyl carbon under activating conditions; can be transformed to isocyanates, carbamates, thioureas, or N‑acyl/sulfonyl ureas.
Secondary alcohol at C4: convertible to halides/sulfonates (leaving groups), oxidizable to ketone, or protected as silyl/carbonate. Enables divergent C4 diversification.
Named/typical transformations (literature)
Mitsunobu (inversion) on the secondary alcohol to install sensitive nucleophiles with stereochemical control (if chirality is introduced).
TEMPO/bleach or Swern oxidation to 4‑piperidone‑1‑carboxamide, followed by reductive amination (NaBH3CN, H2/Pd, or BH3·THF) to generate 4‑alkyl/aryl/heteroaryl derivatives.
Mesylation/tosylation then SN2 with azide (→ 4‑azido intermediate) and Staudinger/azide–alkyne click elaborations for linker chemistry.
Urea N‑functionalization: CDI‑mediated coupling with amines/alcohols to build N‑substituted ureas/carbamates; reaction with sulfonyl chlorides to N‑sulfonyl ureas.
Dehydration (POCl3, SOCl2 variants) to generate the corresponding isocyanate for subsequent Curtius‑like or urethane‑forming steps.
Retrosynthetic value
Serves as a convergent node: urea installs polarity and H‑bonding while the C4 handle enables rapid SAR around the piperidine ring. Particularly useful when a nonbasic piperidine core is desired to modulate pKa and distribution.
Target Specificity
Not applicable. This product is a small‑molecule building block, not a biological macromolecule or affinity reagent. No antigen/epitope/clone or species reactivity applies.
We use cookies to ensure the website functions properly and, where permitted, to improve your experience. You can manage your preferences at any time in Settings. Learn more in our Cookie Policy.
Shall we send you a message when we have discounts available?
Remind me later
Thank you! Please check your email inbox to confirm.
Products are supplied to verified businesses, institutions, and qualified professionals for research and development use only. Not for use in humans, animals, diagnosis, or therapy.
