GRADE & PURITYReagent Grade?General reagent-grade purity suitable for most laboratory work. Use as a dependable default when no specific higher grade is required.
This compound belongs to the class of organic compounds known as alkaloids and derivatives. These are naturally occurring chemical compounds that contain mostly basic nitrogen atoms. This group also includes some related compounds with neutral and even weakly acidic properties. Also some synthetic compounds of similar structure are attributed to alkaloids. In addition to carbon, hydrogen and nitrogen, alkaloids may also contain oxygen, sulfur and more rarely other elements such as chlorine, bromine, and phosphorus.
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
Not applicable. No application protocols (e.g., WB, IHC, IF, FC) are associated with this small-molecule reagent. For synthetic applications, refer to the Reaction Conditions and Synthetic Utility sections for general guidance.
Biological Roles
This item is supplied for research and synthetic use; no biological function is assigned to the catalog material.
General context (literature):
Piperidine motifs are prevalent in natural products and synthetic bioactive compounds. The basic nitrogen can influence receptor binding, permeability, and pKa-dependent ionization in medicinal chemistry.
Ether-functionalized side chains are often used to tune polarity and solubility without adding additional heteroaromatic complexity.
Relevance: 2-(3-Methoxypropyl)piperidine is primarily used as a building block to construct ligands, intermediates, and analog libraries. Any biological activity would derive from target scaffolds into which it is incorporated rather than from the free amine itself.
No clinical or diagnostic uses are implied or supported for this product (research use only).
Buffer Applications
Not typically used as a defined buffer component. As a secondary amine, it can transiently buffer near the pKaH of piperidine (~11), but this is not standard practice for biochemical buffers.
Practical note: If pH control is needed in reactions, use conventional buffer systems (e.g., acetate pH 4–5.5, phosphate pH 6–8, carbonate pH 9–10). For amine-involving reactions, mild acid (AcOH) or base (NEt3/DIPEA) is commonly used instead of true buffers.
Green Alternatives
While the substance itself is a building block, greener choices can be made around its use.
Greener solvent choices (literature guidance):
Prefer 2‑MeTHF or EtOAc over DCM/THF where feasible (e.g., for acylations and extractions).
Use MeOH/EtOH/iPrOH for reductive aminations instead of higher-toxicity solvents.
Replace DMF/NMP with MeCN, propylene carbonate, CPME, or 2‑MeTHF when reaction compatibility allows.
Safer reagents:
Reductive amination: choose NaBH(OAc)3 or catalytic hydrogenation over NaBH3CN to avoid cyanide waste where compatible.
Couplings: employ green coupling reagents (e.g., DMTMM, CDI) in place of HATU/HBTU when possible.
Workup/purification:
Favor aqueous workups and salt-switch crystallizations (e.g., isolate as HCl salt) to reduce silica usage and solvent-intensive chromatography.
Comparison (illustrative):
DCM vs EtOAc: EtOAc is biorenewable-friendly and less hazardous; comparable solubility for many acylations, though DCM may offer faster phase disengagement.
THF vs 2‑MeTHF: 2‑MeTHF has higher boiling point, partial water immiscibility, and improved safety profile; both support similar chemistry.
Note: Always balance green metrics with reaction performance and safety. Validate substitutions at small scale first.
Pharmaceutical Uses
No excipient or clinical application is specified for this item. For research use only.
Literature/general context:
Frequently used as a medicinal chemistry intermediate to introduce a piperidinyl-ether side chain into candidate molecules via amide, carbamate, urea, or sulfonamide linkages.
The formation of crystalline salts (e.g., HCl, fumarate, maleate) is common for handling and can assist in API intermediate isolation during route development.
Regulatory status: No pharmacopeial grade or monograph is indicated. If a regulated process requires it, specifications must be defined and controlled via an internal CoA/Spec aligned to ICH Q7/Q11 expectations for intermediates.
Physical Properties
Item-specific specifications: Not specified for this item; refer to CoA/Spec Sheet.
Literature/general expectations for this structure (for planning only; verify experimentally):
Physical state: likely colorless to pale yellow liquid (typical for low‑MW 2‑substituted piperidines)
Basicity: pKaH (conjugate acid of piperidine) typically ~11.0–11.5 (literature, varies with substitution). Free-base pKa (of the ammonium) corresponds to pKb ~3.5–4.
Boiling range: secondary piperidines of similar MW commonly boil in the ~180–215 °C range at 1 atm (literature trend; specific BP for this CAS not widely reported).
Density: often ~0.85–0.92 g/mL at 20–25 °C for analogous 2-alkyl/alkoxyalkyl piperidines (literature trend).
Refractive index: typically nD20 ~1.45–1.48 for comparable amino ethers (literature trend).
Solubility: miscible with many organic solvents (EtOAc, alcohols, ethers, hydrocarbons). Expected partial miscibility with water due to one tertiary amine and one ether oxygen; protonated salts are water‑soluble.
Volatility/odor: amine-like odor; moderate vapor pressure compared to smaller amines.
Notes: Values above are generalized literature expectations for closely related structures and are provided for method development only. They are not item-specific specifications.
Quality and Grades
Grade declared for this item: Reagent Grade (from Product Data).
What Reagent Grade typically implies (general guidance):
Suitable for routine synthetic and analytical laboratory work where high purity is required but not necessarily to chromatographic (HPLC/GC) or trace-metal specifications.
Typical controls include identity confirmation (e.g., NMR/IR), assay by GC/HPLC, and limits on common impurities/residual solvents appropriate for research use. Exact acceptance criteria vary by manufacturer.
What is not specified for this item: water content, stabilizers/inhibitors, trace metals, GC/HPLC area %, UV cutoff — Not specified for this item; refer to CoA/Spec Sheet.
Practical implications:
For moisture/air‑sensitive transformations, consider verifying assay and water by Karl Fischer on the received lot.
If using in catalysis or medicinal chemistry SAR, further purification (distillation or column) may be performed as needed to meet in‑house specs.
Research Use Only notice: For research use only (per Product Data). Not for food, drug, household, or diagnostic use.
Reaction and Applications
2-(3-Methoxypropyl)piperidine is a versatile secondary amine bearing an ether side chain. It serves as a nucleophile, base, and medicinal chemistry building block.
Representative applications (literature/general):
Amide/urea/carbamate formation: couples readily with acid chlorides, activated esters, anhydrides, CDI, or carbamoyl chlorides to give piperidinyl amides/ureas/carbamates.
Reductive amination: couples with aldehydes/ketones to install additional substituents at nitrogen; NaBH3CN or NaBH(OAc)3 in MeOH/MeCN buffers the medium around pH 5–6 for selectivity.
N‑alkylation (SN2/Williamson-type): reacts with alkyl halides/mesylates under basic conditions; use polar aprotic solvents (MeCN/DMF) and inorganic bases (K2CO3/Cs2CO3). Ether side chain is generally inert under SN2 conditions.
Salt formation and phase-transfer: protonated forms can act as phase-transfer catalysts in certain nucleophilic substitutions (quaternization possible with MeI/EtI).
Cyclizations/heterocycle elaboration: the β/γ-alkoxy side chain permits intramolecular reactions after suitable activation (e.g., to tosylate), enabling oxygen–nitrogen tether strategies.
Cross-coupling adjunct: forms amide linkages to aryl acids for PROTAC-like linkers; can be introduced into scaffolds via coupling to chloroformates or NHS esters.
Practical tips:
Maintain mildly basic conditions to keep the amine free; add 1–2% NEt3 to chromatography eluents to minimize tailing.
For acylations, pre-form the corresponding HCl salt to manage exotherm, then liberate the free base in situ with base.
Hydrogenation-sensitive substrates: the ether substituent is stable under Pd/C H2, but protect any other reducible groups accordingly.
Reaction Conditions
General literature guidance for common transformations involving 2‑substituted piperidines (optimize for your substrate; values are indicative, not specifications):
Amide formation (acyl chloride route):
Solvent: DCM, THF, or 2‑MeTHF
Base: DIPEA (2–3 equiv) or NaHCO3 (aq biphasic)
Temperature: 0 °C → rt, 1–3 h; typical isolated yields 70–95% with clean electrophiles.
Carbamate formation (chloroformate):
Solvent: DCM or MeCN; base: pyridine or NEt3 (2–3 equiv)
Temperature: 0–25 °C; 1–2 h; often >80% yield.
Reductive amination:
Solvent: MeOH, iPrOH, or MeCN; additives: AcOH (0.2–0.5 equiv)
Reductant: NaBH(OAc)3 (1.5–2.5 equiv) at rt, 2–16 h; or H2 (1–5 bar) over 5–10% Pd/C in MeOH/EtOH at rt–40 °C.
N‑Alkylation (SN2):
Solvent: MeCN or DMF; base: K2CO3/Cs2CO3 (2–3 equiv)
Electrophiles: primary halides/mesylates; 40–80 °C, 4–24 h; monitor for over-alkylation.
Sulfonamide formation:
Solvent: DCM; base: NEt3 (2–3 equiv)
Temperature: 0–25 °C; 1–3 h.
Workup/purification tips:
Include 1–2% NEt3 or 0.5–1% NH4OH in silica eluents to reduce tailing.
For salt isolation, dissolve crude in Et2O/MTBE and gas with HCl or add ethanolic HCl; filter and dry.
All conditions above are representative literature practices for secondary aliphatic amines and should be re-optimized for the specific substrate set.
Safety and Handling
Item-specific hazard data (GHS, H‑statements, pictograms): Not specified for this item; refer to SDS.
General safety profile for secondary aliphatic amines (literature/guidance; defer to SDS):
Hazards: irritant/corrosive to skin, eyes, and respiratory tract; may be harmful if swallowed or inhaled. Amines can form salts with acids and may absorb CO2 from air.
Incompatibilities: strong oxidizers; strong acids (exothermic neutralization and salt formation); acylating agents; acid chlorides/anhydrides (vigorous acylation); isocyanates and epoxides (addition reactions). Avoid copper/brass during storage of neat amines.
PPE: chemical-resistant gloves (e.g., nitrile), lab coat, splash goggles; use in a fume hood.
Handling: minimize exposure to air to limit CO2 uptake and potential discoloration; keep containers tightly closed. Ground/bond if transferring bulk liquids.
First aid (overview; consult SDS for full guidance):
Inhalation: move to fresh air; seek medical attention if symptoms persist.
Skin/eye contact: rinse with plenty of water for ≥15 min; remove contaminated clothing; get medical advice.
Ingestion: rinse mouth; do not induce vomiting; seek medical attention.
Spill response: absorb with inert material (vermiculite, spill pads). Neutralize residues cautiously with dilute acid, then collect as hazardous waste.
Always consult the official SDS for this catalog item before use.
Solvent Selection
This product is a basic organic building block, not a solvent. Solvent choice should be optimized for its use in synthesis, purification, or analysis.
Polarity/acid–base considerations (general):
The secondary amine is readily protonated; in protic media (MeOH, EtOH) it forms ammonium species and shows enhanced water miscibility.
Nonprotic polar solvents (MeCN, DMF, DMSO, 2‑MeTHF, EtOAc) dissolve it well and are preferred for acylation, alkylation, and reductive amination.
Typical selections by transformation:
Acylation/carbamate formation: DCM, THF, 2‑MeTHF, EtOAc, or MeCN with base (Et3N, DIPEA, NaHCO3).
Reductive amination: MeOH, EtOH, iPrOH, or MeCN with NaBH3CN, NaBH(OAc)3, or catalytic hydrogenation (Pd/C) under mild acid buffering.
N‑alkylation/SN2: acetonitrile, acetone, DMF, or MeCN with K2CO3/Na2CO3; avoid strong protic solvents that quench nucleophilicity.
Purification solvents:
Flash chromatography: gradients of hexanes/EtOAc with 1–2% NEt3 to suppress streaking; or DCM/MeOH with 0.5–1% NH4OH.
Distillation: feasible if a clean boiling point gap exists; use a short‑path with base-washed glassware to minimize wall-catalyzed discoloration.
Salts to aid handling: Forming the HCl or p‑TsOH salt can enhance crystallinity and ease purification; choose alcohols/EtOAc/MTBE as crystallization media.
Storage and Reconstitution
Item-specific storage: Room temperature (from Product Data).
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 guidance (literature/practice):
Store tightly closed in a dry, well-ventilated place away from strong acids and oxidizers. Amines can absorb CO2 and moisture; consider flushing headspace with inert gas for long-term storage.
If discoloration occurs over time, material can often be purified by distillation under reduced pressure or converted to a crystalline salt (e.g., HCl) and recrystallized.
No reconstitution is normally required; supplied as a neat compound. If a solid salt form is prepared, dissolve in suitable anhydrous solvent (e.g., MeOH, EtOH, MeCN) as needed.
Stability: Secondary aliphatic amines are generally stable at ambient conditions in the absence of light/air contaminants. Always verify integrity by NMR/GC before use in critical applications.
Structure and Identity
Brief description: 2-(3-Methoxypropyl)piperidine is a secondary amine featuring a saturated six‑membered piperidine ring bearing a 3‑methoxypropyl substituent at the 2‑position (α to nitrogen). The molecule presents one basic tertiary center (ring nitrogen) and one ether oxygen.
Item-specific identifiers (from Product Data):
CAS: 915922-77-9
PubChem CID: 4712039
InChIKey: 434943 (as provided)
SMILES: Not specified for this item; refer to CoA/Spec Sheet.
Literature/computed identity details (general reference information, not item-specific specs):
Structural features (2D description): a chair-like piperidine ring (one nitrogen, five carbons). At C-2 (adjacent to N), a –CH2–CH2–CH2–O–CH3 substituent extends; the terminal methoxy is connected via an ether linkage. No defined stereocenter in the name; the 2‑substituted ring carbon can be chiral if substituted asymmetrically, but this product is not specified as chiral-enriched.
Key reactivity derives from the secondary amine (nucleophilicity/basicity) and the terminal methoxy ether (stable, polarity‑enhancing handle).
Transformations (literature):
N‑Acylation/Carbamylation: with acyl chlorides, anhydrides, activated esters (EDC/HOBt, DIC/oxyma, CDI); forms amides/carbamates for SAR exploration.
N‑Alkylation: SN2 on primary halides/mesylates; use Cs2CO3/K2CO3 in MeCN/DMF; phase-transfer catalysis possible. Quaternization yields piperidinium salts.
Reductive amination: condense with carbonyls; reduce with NaBH(OAc)3 (AcOH-buffered) or hydrogenation (Pd/C, H2 1–5 bar).
Sulfonylation: with sulfonyl chlorides (NEt3, DCM) to give sulfonamides.
Side-chain derivatization: convert –OCH3 to a leaving group via demethylation (e.g., BBr3/AlCl3 for aryl ethers is not suitable; for alkyl methyl ethers, use iodocyclohexane/HI or Lewis acid mediated cleavage), or activate the adjacent carbon (e.g., tosylate formation after O→OH exchange). Alternatively, replace the methoxypropyl tether by SN2 using a haloalkoxy precursor during synthesis.
Salt switches/crystallization: form HCl or p‑TsOH salts to enhance stability/handling and enable solid-phase purifications.
Retrosynthetic value: Serves as a masked polar appendage donor; the piperidine can be disconnected to acid derivatives (for amide coupling) or to electrophiles amenable to SN2 from the amine.
Target Specificity
Not applicable. This product is a small-molecule building block and is not an antibody, enzyme, or affinity reagent. No biological target, epitope, isotype, or species reactivity is defined.
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