27262-43-7

Basic information

• Product Name: (2R)-N-(2,6-DIMETHYLPHENYL)-2-PIPERIDINECARBOXAMIDE
• Synonyms: (2R)-N-(2,6-DIMETHYLPHENYL)-2-PIPERIDINECARBOXAMIDE;N-Despropyl (R)-Ropivacaine;(R)-2',6'-Pipecoloxylidide;(R)-N-(2,6-DiMethylphenyl)-2-piperidinecarboxaMide;N-Desbutyl (R)
• CAS NO: 27262-43-7
• Molecular Formula: C₁₄H₂₀N₂O
• Molecular Weight: 232.325
• Product Categories: Aromatics;Heterocycles;Intermediates & Fine Chemicals;Metabolites & Impurities;Pharmaceuticals;Aromatics, Heterocycles, Metabolites & Impurities, Pharmaceuticals, Intermediates & Fine Chemicals
• Mol File: 27262-43-7.mol
• Article Data: 14

Chemical Properties

• Boiling Point: 392.3±42.0 °C(Predicted)
• Appearance: /
• Density: 1.087±0.06 g/cm3(Predicted)
• PKA: 14.85±0.70(Predicted)
• CAS DataBase Reference: (2R)-N-(2,6-DIMETHYLPHENYL)-2-PIPERIDINECARBOXAMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: (2R)-N-(2,6-DIMETHYLPHENYL)-2-PIPERIDINECARBOXAMIDE(27262-43-7)
• EPA Substance Registry System: (2R)-N-(2,6-DIMETHYLPHENYL)-2-PIPERIDINECARBOXAMIDE(27262-43-7)

Safety Data

• Hazardous Substances Data: 27262-43-7(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 27262-43-7 differently. You can refer to the following data:
1. A major metabolite of (R)-enantiomers of Bupivacaine (B689545) and the anesthetic Ropivacaine (R675005).
2. N-Despropyl (R)-Ropivacaine is a major metabolite of (R)-enantiomers of Bupivacaine (B689545) and the anesthetic Ropivacaine (R675005).

Upstream product

• 110-52-1 1,4-dibromo-butane 
• 102881-97-0 2-amino-N-(2,6-dimethyl-phenyl)-malonamic acid ethyl ester 
• 39627-98-0 2-pyridine-carboxamide-N-(2,6-dimethylphenyl) 
• 87-62-7 2,6-dimethylaniline 
• 1537190-05-8 C₁₄H₂₀N₂O*C₁₆H₁₅NO₃ 
• 636-80-6 2-picolinic acid hydrochloride 
• 67-56-1 methanol 
• 98-98-6 2-Picolinic acid 
• 4043-87-2 pipecolic Acid 
• 28697-07-6 N-benzyloxycarbonyl D/L-pipecolinic acid 
• 27262-40-4 (S)-2',6'-pipecoloxylidide 
• 67-63-0 isopropyl alcohol 
• 100616-40-8 N-(2,6-dimethyl-phenyl)-2-hydroxyimino-malonamic acid ethyl ester 
• 15960-82-4 ethyl 3-((2,6-dimethylphenyl)amino)-3-oxopropanoate 

Downstream Products

• 1364698-38-3 (R,S)-N-(2,6-dimethylphenyl)piperidinium-2-carboxamide bis-(trifluoromethylsulfonyl)imide 
• 27262-40-4 (S)-2',6'-pipecoloxylidide 
• 78289-28-8 pipecolic-2-acid-2',6'-xylidide 
• 14252-80-3 bupivacaine hydrochloride 
• 98626-61-0 1-propyl-N-(2,6-dimethylphenyl)piperidine-2-carboxamide 

Relevant articles and documents

Synthesis, biological evaluation, and molecular docking of ropivacaine analogs as local anesthetic agents

Two series of ropivacaine analogs (4a–4q, 7a–7c) were synthesized, and their biological activities were evaluated as local anesthetic agents. Most of the compounds displayed detectable local anesthetic characteristics. Among them, compound 4l showed significant efficacy with sciatic nerve block, infiltration, corneal surface, and spinal anesthetic activities. It was as potent as the reference compound ropivacaine. Dissociation constants of these compounds were 5.9–7.9. In addition, molecular docking modeling on compound 4l and ropivacaine was performed to delineate structural requirements and potential mechanisms for the local anesthetic activity. This study provides valuable new information for our ongoing endeavor to design more potent local anesthetics.

Synthesis of Mepivacaine and Its Analogues by a Continuous-Flow Tandem Hydrogenation/Reductive Amination Strategy

Herein we report a convenient, fast, and high-yielding method for the generation of the racemic amide anaesthetics mepivacaine, ropivacaine, and bupivacaine. Coupling of α-picolinic acid and 2,6-xylidine under sealed-vessel microwave conditions generates the intermediate amide after a reaction time of only 5 min at 150 °C. Subsequent reaction in a continuous-flow high-pressure hydrogenator (H-Cube ProTM) in the presence of the respective aldehyde directly converts the intermediate to the final amide anaesthetics in a continuous, integrated, multi-step ring-hydrogenation/reductive amination protocol. Merits and limitations of the protocol are discussed.

A process for the preparation of ropivacaine hydrochloride

The invention provides a method for preparing hydrochloric acid ropivacaine. Part of parameters and conditions in the prior art are improved, and optimization is performed through the following steps that intermediate (I) separation pH and separation extracting solvent are selected; a catalyst and the usage quantity of the catalyst in a resolution agent are selected; refining solvent is selected. In this way, the yield and purity of the prepared hydrochloric acid ropivacaine are high, the purity reaches up to over 99% under the optimal condition, the percentage of dextrorotary isomer is reduced below 0.5%, standard requirements are completely met, and the hydrochloric acid ropivacaine is suitable for industrial production.