Chemical Identity and Structure

Benzyl 4-aminopiperidine-1-carboxylate hydrochloride (SKU: B189850) is the hydrochloride salt of a piperidine derivative bearing two orthogonally addressable nitrogen functionalities. The nitrogen at the 1-position of the piperidine ring is protected as a benzyloxycarbonyl (Cbz) carbamate, while the nitrogen at the 4-position exists as a free primary amine — protonated as its hydrochloride salt in the commercial form. This dual-nitrogen architecture makes it a highly valuable bifunctional building block in multi-step synthesis.

The Cbz (Z) protecting group on N-1 is removable under mild hydrogenolysis conditions (H₂, Pd/C) or by treatment with strong Lewis or Brønsted acids, offering flexibility in deprotection strategy. The 4-amino group, once free-based from the HCl salt, is available for acylation, reductive amination, sulfonylation, and coupling reactions without disturbing the carbamate.

Applications in Medicinal Chemistry

The compound serves as a key intermediate in the synthesis of pharmacologically active molecules, particularly kinase inhibitors, GPCR modulators, and CNS-targeted agents, where the piperidine ring is a privileged scaffold. The 4-aminopiperidine motif is found in numerous approved drugs and clinical candidates owing to its favorable pharmacokinetic properties, including adequate aqueous solubility and metabolic stability.

Typical synthetic transformations employing B189850 include:

• Amide bond formation: Coupling of the free-based 4-amino group with activated carboxylic acids or acyl chlorides using standard coupling reagents (e.g., HATU, EDC/NHS) in DMF or DCM.
• Reductive amination: Condensation with aldehydes or ketones followed by reduction with NaBH(OAc)₃ or NaBH₄.
• Sulfonylation: Reaction with sulfonyl chlorides in the presence of a tertiary amine base (e.g., Et₃N, DIPEA) to install sulfonamide groups.
• Cbz deprotection then N-functionalization: Sequential removal of the Cbz group and subsequent functionalization of the ring nitrogen for scaffold diversification.

The hydrochloride salt form ensures enhanced stability and ease of weighing compared to the free base.

Handling, Safety, and Storage Guidelines

Personal Protective Equipment (PPE): Handle with appropriate PPE including nitrile gloves, safety glasses, and a lab coat. Conduct all weighing and solution preparation in a well-ventilated fume hood to avoid inhalation of dust. As a hydrochloride salt containing a primary amine, it may be a mild irritant to skin, eyes, and respiratory tract.

Storage: Store at 2–8 °C in a tightly sealed container under dry conditions, protected from light. Prolonged exposure to moisture may promote hydrate formation or deliquescence, potentially affecting assay accuracy. Upon receipt, inspect the material for any discoloration or caking; such changes may indicate degradation.

Reconstitution and Solution Preparation: The compound is freely soluble in water and common polar aprotic solvents such as DMSO and DMF. For reactions requiring the free base, treat an aqueous solution with a dilute base (e.g., Na₂CO₃ or K₂CO₃) and extract with an organic solvent such as ethyl acetate or DCM prior to use. Prepare stock solutions fresh or in aliquots to minimize freeze-thaw cycles.

Waste Disposal: Dispose of chemical waste in accordance with local, national, and institutional regulations. Do not pour solutions down the drain without confirming compliance with applicable waste management guidelines.

Quality Specifications and Analytical Characterization

Aladdin Scientific's B189850 is manufactured and quality-controlled to meet research-grade standards. Typical characterization data for this compound include:

• Appearance: White to off-white crystalline powder
• Purity: ≥97% by HPLC (verify current lot certificate of analysis for exact value)
• Identity confirmation: ¹H NMR and ¹³C NMR consistent with proposed structure; IR spectrum showing characteristic N–H stretch (~3300 cm^-1), C=O carbamate stretch (~1690 cm^-1), and N–H bend of ammonium salt
• Mass spectrometry: ESI-MS m/z consistent with [M+H]⁺ of the free base (MW 234.30 g/mol)

Users should request a Certificate of Analysis (CoA) for each lot. Parameters to review include purity by HPLC, water content (Karl Fischer titration), and residual solvents if applicable. Contact Aladdin Scientific technical support for lot-specific data or if specifications beyond standard CoA parameters are required for regulatory or GMP-adjacent applications.

Ordering and Regulatory Information

Benzyl 4-aminopiperidine-1-carboxylate hydrochloride (B189850) is available through Aladdin Scientific for research and development use only. It is not intended for diagnostic, therapeutic, or human consumption purposes.

Ordering: Place orders via the Aladdin Scientific website, by contacting your regional sales representative, or through approved procurement portals. Bulk quantities may be available upon request; lead times for non-standard pack sizes should be confirmed at the time of inquiry.

Regulatory status: This compound is not currently listed as a controlled substance under common international regulatory frameworks; however, end-users are responsible for verifying compliance with all applicable local regulations before purchase and use. Import/export regulations may apply depending on destination country.

Return and quality claims: In the event of quality concerns (damaged packaging, out-of-specification material), contact Aladdin Scientific customer service within the stated return window, referencing the lot number and order number. For full return and refund policy details, consult the Aladdin Scientific website.