Cyclohexanone, 4-(1-piperidinyl)- , CAS No.60481-62-1

CAS: 60481-62-1 Cat. No.: C978585 Fórmula: C₁₁H₁₉NO Peso molecular: 181.270

Storage

Room temperature

Specifications

Condiciones de almacenamiento de almacenamiento

Room temperature

Nombres e identificadores

• Sonrisas canónicas: C1CCN(CC1)C2CCC(=O)CC2
• IUPAC Name: 4-piperidin-1-ylcyclohexan-1-one
• InChIKey: ZNDMWZIAZJLETD-UHFFFAOYSA-N
• INCHI: 1S/C11H19NO/c13-11-6-4-10(5-7-11)12-8-2-1-3-9-12/h10H,1-9H2
• Peso molecular: 181.270

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organoheterocyclic compounds
    • Clase Piperidines

• Kingdom: Organic compounds
• Superclass: Organoheterocyclic compounds
• Clase: Piperidines
• Subclass: Not available
• Intermediate Tree Nodes: Not available
• Direct Parent: Piperidines
• Alternative Parents: Trialkylamines Cyclic ketones Azacyclic compounds Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aliphatic heteromonocyclic compounds
• Substituents: Piperidine - Cyclic ketone - Tertiary aliphatic amine - Tertiary amine - Ketone - Azacycle - Organic nitrogen compound - Organic oxygen compound - Organic oxide - Hydrocarbon derivative - Organooxygen compound - Organonitrogen compound - Carbonyl group - Amine - Aliphatic heteromonocyclic compound
• Descripción: 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

Data sources

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.

DOI: 10.1186/s13321-016-0174-y

Propiedades químicas y físicas

• Peso molecular: 181.270 g/mol
• XLogP3: 1.300
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 181.147 Da
• Monoisotopic Mass: 181.147 Da
• Topological Polar Surface Area: 20.300 Ų
• Heavy Atom Count: 13
• Formal Charge: 0
• Complexity: 175.000
• 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

Application Protocols

No assay or immunoapplication protocols are defined for this small-molecule reagent. For chemical use, consider the following general preparation approaches:

• Stock solutions: Prepare 10–100 mM stocks in dry DMSO or acetonitrile; filter through 0.22 µm PTFE if particulate is present.
• Salt formation for aqueous work: Dissolve in minimal Et2O or MeOH and treat with dry HCl in dioxane to precipitate the hydrochloride salt; isolate and dry under vacuum.
• Analytical methods: Monitor reactions by LC–MS (ESI+, track [M+H]+ ~183 as a literature/computed value), TLC with basic modifiers (1–2% Et3N) to prevent streaking of the amine.

For any validated, product-specific protocols, consult the CoA/Spec Sheet.

Biological Roles

This product is a synthetic organic intermediate and is provided strictly for research use. No biological activity or clinical utility is claimed for this catalog item.

General biochemical context (literature, not product-specific claims):

• Piperidine is a common motif in bioactive molecules, contributing basicity (conjugate acid pKa typically ~10–11) and aqueous salt-forming capability. Such tertiary amines can influence membrane permeability and receptor binding in diverse scaffolds.
• The cyclohexanone carbonyl can serve as a handle for generating imines/enamines in biochemical probe synthesis or for conjugation strategies that target nucleophilic residues in biomolecules under controlled conditions (e.g., forming reversible imine linkages that can be reduced to stable amines).
• As a tertiary amine, the free base can be protonated to give water-soluble ammonium salts, facilitating formulation in assay buffers at low millimolar concentrations after DMSO predissolution.

Caution: Any biological testing must be conducted under appropriate approvals and safety protocols. For all toxicological and exposure information, consult the SDS; do not infer therapeutic relevance from the presence of common pharmacophores.

Buffer Applications

This compound is not a conventional buffering reagent. While tertiary amines can accept protons (conjugate acid pKa typically in the ~10–11 range for piperidines), 4-(piperidin-1-yl)cyclohexanone is not used as a standardized buffer component.

Practical notes (general):

• For biological assays, prepare stock solutions in DMSO and dilute into the desired buffer (e.g., PBS, HEPES) while controlling pH. If higher aqueous solubility is needed, form an acid salt (e.g., HCl salt) ex situ and adjust to the target pH.
• Avoid relying on this compound for pH control; select established systems (HEPES, TRIS, phosphate) appropriate to the required pH range.

Refer to the SDS and CoA for any solubility and compatibility constraints specific to this item.

Green Alternatives

As a reagent/building block, greener practice focuses on solvent and process choices rather than replacing the molecule itself.

Greener solvent choices for typical operations (general guidance):

• Dissolution/workup: Prefer ethyl acetate, 2-MeTHF, or CPME over chlorinated solvents when feasible; these often provide adequate solubility and improved EHS profiles.
• Reductive amination: Use ethanol or 2-propanol as solvent/hydrogen donor with catalytic hydrogenation (Pd/C) to avoid stoichiometric borohydrides.
• Oxime formation/carbonyl derivatization: Employ aqueous ethanol with catalytic acid instead of neat strong acids; manage pH to keep the amine protonated (reducing odor and volatility).

Illustrative comparison (general):

• DCM vs EtOAc: EtOAc is biodegradable and has lower toxicity; DCM offers superior volatility and solubility. If rate/solubility allow, choose EtOAc.
• THF vs 2-MeTHF: 2-MeTHF (from renewable feedstocks) reduces peroxide hazard, has higher boiling point, and better water immiscibility; THF is more ubiquitous and sometimes higher-reactivity due to polarity.
• MeCN vs CPME: CPME can replace MeCN in some cases with favorable safety; MeCN offers greater polarity and is excellent for many base-mediated reactions.

Waste minimization:

• Exploit the amine’s acid–base properties for efficient phase separations to reduce chromatography.
• Telescoping: Combine imine/oxime formation and subsequent reduction without isolation when selectivity allows.

Pharmaceutical Uses

No excipient or pharmacopeial status is specified for this item; refer to CoA/Spec Sheet. This product is offered for research use only and is not intended for human or veterinary use.

General formulation-relevant considerations for tertiary amine ketone building blocks (literature/practice):

• Salt formation: The tertiary amine can be converted to pharmaceutically acceptable salts (e.g., HCl, mesylate) to enhance crystallinity and aqueous solubility during pre-formulation studies.
• Solid-state screening: Carbonyl–amine scaffolds often exhibit multiple polymorphs/salts; early screening can improve developability metrics in discovery support, though no claims are made for this specific item.
• Impurity control: Monitor for oxidation or N-alkylation byproducts under stress. Use inert atmosphere and light protection as needed in forced-degradation studies.

Note: This section provides general development context only. Do not construe it as a claim of suitability for clinical or GMP manufacturing. Always consult quality documents and regulatory guidance for intended use.

Physical Properties

Item-specific specifications (this SKU):

• Appearance: Not specified for this item; refer to CoA/Spec Sheet.
• Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.

Literature/computed properties for 4-(piperidin-1-yl)cyclohexanone (informational, not product specs):

• Molecular formula: C11H20NO (computed from structure)
• Molecular weight: ~182.29 g/mol (computed)
• Acid–base: tertiary amine; expected pKaH of conjugate acid typically ~10–11 for piperidines (literature range; exact value depends on substitution and medium)
• LogP: tertiary amine–ketone scaffolds of this size often show moderate lipophilicity (literature expectation); exact value not specified
• Solubility: generally soluble in common organic solvents (e.g., dichloromethane, ethyl acetate, alcohols, acetone); free base may exhibit limited water solubility but increased solubility under acidic conditions as the ammonium salt (general observation for tertiary amines)
• Physical state: typically a liquid or low-melting solid/oil for analogous tertiary amine ketones; exact MP/BP not specified for this item
• Boiling point, melting point, density, refractive index, UV cutoff: Not specified for this item; refer to CoA/Spec Sheet.

Note: Use the batch-specific CoA for any property required for regulatory filings or method validation.

Quality and Grades

• Item-specific grade/purity: Not specified for this item; refer to CoA/Spec Sheet.

Guidance on interpreting grades (general):

• Research grade: Suitable for most synthetic, screening, and discovery workflows. Purity is typically defined by NMR/GC/LC but may allow trace residual solvents or inorganic impurities.
• ≥98–99% (typical high-purity benchmarks in catalogs): Indicates low levels of organic impurities; useful for structure–activity studies or when downstream purification is undesirable. If UV-trace/LC-trace grades are offered, they are optimized for chromatographic uses with controlled UV background.
• Stabilizers: Not specified for this item; refer to CoA/Spec Sheet. Tertiary amines generally do not require inhibitors; however, carbonyl-containing amines can slowly oxidize—antioxidants are rarely added, but inert-atmosphere storage is beneficial for analytical-critical applications.

What to check on the CoA for this molecule:

• Identity: 1H/13C NMR consistent with a tertiary amine and cyclohexanone carbonyl; HRMS for [M+H]+ ≈ 183.3 (computed, literature); IR carbonyl near ~1715 cm⁻¹ (literature) alongside C–N stretches.
• Purity method: GC or LC purity and residual solvent content.
• Water content: Not specified for this item; refer to CoA/Spec Sheet.
• Trace metals/UV cutoff: Not specified for this item; refer to CoA/Spec Sheet.

Reaction and Applications

Use domains (general for 4-(piperidin-1-yl)cyclohexanone-like scaffolds):

• Building block for piperidine-bearing libraries and CNS-privileged motifs; tertiary amine facilitates salt formation for isolation, while the cyclohexanone carbonyl provides orthogonal reactivity.
• Precursor in diversity-oriented synthesis: The carbonyl undergoes reductive amination, oxime/hydrazone formation, or Wittig/olefination to furnish substituted amines/alkenes while retaining the tertiary amine center.
• Alpha-functionalization: Enolization enables halogenation, alkylation, or oxidations (e.g., via LDA, NaH, or organocatalysis); the pendant tertiary amine can direct or modulate reactivity via enamine formation.
• Quaternization and salt chemistry: Alkylation of the tertiary nitrogen yields quaternary ammonium salts useful as phase-transfer catalysts or ionic intermediates.
• Conjugate additions: If transient enone is generated (via oxidation/dehydrogenation), Michael additions can diversify the scaffold.

Practical tips:

• Drying: If required anhydrous, dry over K2CO3 or 4 Å molecular sieves; avoid strong drying acids (will protonate the amine).
• Protecting groups: The tertiary amine cannot be acyl-protected; for carbonyl protection, form ketals (e.g., ethylene glycol, acid-catalyzed), noting the amine must be protonated to avoid basic inhibition of acid catalysis.
• Workups: Take advantage of acid–base extraction (protonate to transfer into aqueous, basify to liberate free base back into organic phase).
• Analytics: LC–MS readily detects [M+H]+ ~183; monitor carbonyl transformations by IR (C=O ~1715 cm⁻¹, literature) and NMR (C=O ~δC 210 ppm).

Reaction Conditions

General literature guidance for common transformations of tertiary amine–ketone scaffolds (not product specifications):

• Reductive amination of the cyclohexanone:

  • Typical conditions: Amine partner (RNH2 or R2NH), NaBH3CN or NaBH(OAc)3 in MeOH/HOAc or DCE with molecular sieves; 0–25 °C, 2–16 h. Catalytic hydrogenation (Pd/C, H2 1–5 bar) in EtOH/i-PrOH as a greener alternative.
  • Notes: The tertiary piperidine remains unreactive toward imine formation but may need protonation (AcOH) to reduce basic inhibition.

• Oxime formation/hydrazone:

  • Hydroxylamine·HCl or hydrazine derivatives, EtOH/H2O, catalytic acid, rt–60 °C, 1–6 h. Monitor by IR/NMR for loss of C=O.

• α-Halogenation/alkylation:

  • Enolization with LDA or LiHMDS in THF/THF–hexanes, −78 to 0 °C; trap with electrophiles (MeI, benzyl bromide) or NBS/NCS for halogenation. Quench and extract via acid–base workup to remove amine-derived salts.

• Ketal protection:

  • Ethylene glycol, catalytic p-TsOH in toluene with Dean–Stark, reflux 2–6 h. Protonate the tertiary amine beforehand to avoid neutralizing the acid catalyst.

• Quaternization of the amine:

  • Alkyl halide (e.g., MeI, BnBr), MeCN or acetone, rt–50 °C, 2–24 h. Isolate as crystalline ammonium salts.

Yields and exact parameters vary with substrate and substituents; consult primary literature and optimize on small scale.

Safety and Handling

Item-specific hazard data:

• GHS Classification: Not specified for this item; refer to SDS.
• Signal Word / H-Statements / Pictograms: Not specified for this item; refer to SDS.

General safety guidance for tertiary amine ketones (literature/industry practice):

• Likely hazards: May cause skin/eye irritation and respiratory irritation; tertiary amines can be corrosive to some plastics and may have strong odor. Avoid inhalation of vapors and contact with skin/eyes.
• PPE: Use appropriate lab coat, nitrile gloves, and splash goggles. Work in a chemical fume hood to minimize vapor/aerosol exposure.
• Handling: Keep containers tightly closed. Minimize exposure to air/CO2; tertiary amines can absorb CO2 forming carbamates at the surface. Avoid contact with strong oxidizers, strong acids (will form ammonium salts exothermically), and acylating/alkylating agents.
• Incompatibilities: Strong oxidizing agents, acid chlorides/anhydrides, and strong mineral acids. Carbonyl functionality can undergo nucleophilic addition; avoid unintended reactive mixtures with strong bases/nucleophiles without controls.
• First aid overview: Skin/eye contact—immediately flush with water for at least 15 minutes; remove contaminated clothing. Inhalation—move to fresh air; seek medical attention if symptoms persist. Ingestion—not intended for consumption; seek medical attention.
• Fire safety: Use CO2, dry chemical, or foam. Amines can be combustible; assess flash point from SDS when available.

Always consult the Aladdin SDS for authoritative, product-specific safety and regulatory information.

Solvent Selection

This product is a small-molecule reagent/building block, not a bulk solvent. Solvent choice pertains to dissolving it for reactions, analyses, or formulations.

General solvent compatibility (literature/experience for tertiary amine ketones):

• Likely good solubility in: dichloromethane (DCM), chloroform, ethyl acetate, acetone, acetonitrile, THF, alcohols (MeOH/EtOH/i-PrOH). Solubility in hexanes may be moderate due to polar functionalities.
• Aqueous systems: The free base typically has limited solubility in neutral water but becomes water-soluble upon protonation (e.g., forming HCl salt). For bioassays, dissolve in DMSO then dilute into buffer with pH control.

Selection tips:

• Base-sensitive transformations: Prefer aprotic solvents (DCM, MeCN, THF) to avoid amine protonation unless the ammonium salt is desired.
• NMR: CDCl3 commonly suitable; if protonation is needed, use CD3OD or add a drop of TFA-d.
• Workup: The basic nitrogen facilitates acid–base extraction; choose biphasic systems (e.g., DCM/aqueous HCl) for efficient partitioning.

Small comparison (general):

• DCM vs EtOAc: DCM offers higher solubility and easier phase splits; EtOAc is a greener alternative but may give slower reactions for some nucleophilic steps.
• MeCN vs THF: MeCN is polar aprotic and facile to dry; THF enhances nucleophilicity but can solvate bases more strongly.

Storage and Reconstitution

• Storage conditions (from Product Data): Room temperature.
• Shipped in: Not specified for this item; refer to CoA/Spec Sheet.
• Appearance: Not specified for this item; refer to CoA/Spec Sheet.

General handling and storage guidance for tertiary amine ketones:

• Keep tightly closed in an inert container; minimize air exposure to limit CO2 uptake and odor. If long-term storage is planned, consider nitrogen backfill.
• Protect from strong light and oxidants. Avoid contact with acidic vapors to prevent salt formation on the container surfaces.
• If solidification/crystallization occurs on cooling, redissolve gently at ambient temperature or in a small amount of compatible solvent (e.g., DCM, EtOAc) and use as required.
• Reconstitution: If supplied as a neat liquid/solid, no reconstitution is required. For solution preparations, dissolve in dry DMSO, MeCN, EtOH, or DCM to the desired concentration. Filter sterilize through PTFE for bioassay use if necessary.
• Freeze–thaw: Not generally required. If preparing aliquots of solutions, store sealed to prevent evaporation and adsorption; avoid repeated opening to limit moisture uptake.

Research Use Note: For research use only.

Structure and Identity

Brief description: Cyclohexanone, 4-(1-piperidinyl)- is a tertiary amine–ketone bifunctional small molecule featuring a piperidin-1-yl substituent at the 4-position of a cyclohexanone ring.

• Item-specific identifiers (from Product Data):
  • CAS: 60481-62-1
  • CID (PubChem): 12361785
  • InChIKey: Not specified for this item; refer to CoA/Spec Sheet.
  • SMILES: Not specified for this item; refer to CoA/Spec Sheet.
• Computed/literature structural details (general):
  • Proposed systematic name (IUPAC-style): 4-(piperidin-1-yl)cyclohexan-1-one (literature interpretation of the common name)
  • Functional groups: tertiary aliphatic amine (piperidine), cyclic ketone (cyclohexanone)
  • Ring systems: monocyclic cyclohexanone (C6), monocyclic piperidine (C5N)
  • Stereochemistry: none specified; substitution at C4 of cyclohexanone typically gives conformers but no defined stereocenters
  • 2D structure (described): a six-membered carbocycle bearing a carbonyl at C1 and a –N(piperidinyl) substituent at C4; the pendant piperidine is a saturated six-membered ring containing one tertiary nitrogen
• Empirical formula and formula mass (computed from the assigned structure; literature):
  • Molecular formula: C11H20NO (literature/computed)
  • Molecular weight: ~182.29 g/mol (literature/computed)

Note: Exact structural identifiers for this catalog item (SMILES/InChI) are not specified; consult the CoA/SDS for definitive identity strings.

Synthetic Utility

Functional group leverage:

• Carbonyl (ketone): enables reductive amination, oxime/hydrazone formation, acyl anion equivalents (umpolung), enolate chemistry (α-alkylation/α-halogenation), and protection as ketals.
• Tertiary amine (piperidine): allows quaternization, salt formation (for purification/solubility), and as a non-nucleophilic base under certain conditions (though tertiary amines are nucleophilic toward strong alkylating agents).

Disconnections and diversification (general):

• Reductive amination at C1 generates 4-(piperidin-1-yl)cyclohexylamines, expanding into diamine-rich scaffolds.
• α-Functionalization provides handles for subsequent cross-couplings after halogenation (e.g., α-bromination → substitution/elimination cascades).
• Formation of enamine intermediates (intramolecular with the tertiary amine is disfavored; intermolecular enamines via external secondary amines) can be harnessed in organocatalysis incorporating this ketone as substrate.
• N-Quaternization furnishes ammonium salts useful as phase-transfer catalysts or ionic liquids precursors tuned by the cyclohexanone substituent.

Operational advantages:

• Built-in basic site simplifies extractions and salt toggling during multistep synthesis.
• Orthogonal reactivity: Carbonyl manipulations proceed without protecting the tertiary amine under many conditions; conversely, amine quaternization can be performed without affecting the carbonyl under mild conditions.

Target Specificity

Not applicable. This product is a small-molecule chemical and not a biological affinity reagent. No antigen/epitope/clone/isotype data are relevant. For intended chemical uses, refer to Reaction & Applications and Synthetic Utility sections.