27262-40-4

Basic information

• Product Name: (2S)-N-(2,6-Dimethylphenyl)-2-piperidinecarboxamide)
• Synonyms: (S)-N-(2',6'-dimethylphenl)-2-Piperidine carboxamide;(S)-N-(2',6'-Dimethylphenyl)Piperidine-2-Carboxylic Amide;(S)-(+)-Pipecolinoxylidide;(2S)-N-(2,6-Dimethylphenyl)-2-piperidinecarboxamide);2',6'-Pipecoloxylidide;L-Pipecolic acid 2,6-xylidide;N-Despropyl Ropivacaine;(2S)-N-(2,6-diMethylphenyl)piperidine-2-carboxaMide
• CAS NO: 27262-40-4
• Molecular Formula: C₁₄H₂₀N₂O
• Molecular Weight: 232.32
• EINECS: 1308068-626-2
• Product Categories: Amines;Aromatics;Heterocycles;Intermediates & Fine Chemicals;Metabolites & Impurities;Pharmaceuticals
• Mol File: 27262-40-4.mol

Chemical Properties

• Melting Point: 129-130°C
• Boiling Point: 392°C
• Flash Point: 149°C
• Appearance: /
• Density: 1.087
• Storage Temp.: Refrigerator
• Solubility: DMSO, Methanol (Slightly), Water (Slightly, Heated and Sonicated)
• PKA: 14.85±0.70(Predicted)
• CAS DataBase Reference: (2S)-N-(2,6-Dimethylphenyl)-2-piperidinecarboxamide)(CAS DataBase Reference)
• NIST Chemistry Reference: (2S)-N-(2,6-Dimethylphenyl)-2-piperidinecarboxamide)(27262-40-4)
• EPA Substance Registry System: (2S)-N-(2,6-Dimethylphenyl)-2-piperidinecarboxamide)(27262-40-4)

Safety Data

• Hazardous Substances Data: 27262-40-4(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(2S)-N-(2,6-Dimethylphenyl)-2-piperidinecarboxamide is used as an intermediate in the synthesis of various pharmaceutical compounds. Its unique molecular structure allows it to serve as a building block for the development of new drugs, particularly those targeting the central nervous system.
Used in Chemical Research:
In the field of chemical research, (2S)-N-(2,6-Dimethylphenyl)-2-piperidinecarboxamide is utilized as a research compound for studying the effects of stereochemistry on biological activity. Its specific stereochemistry can provide insights into the development of more effective and selective drugs.
Used in Anesthetic Formulation:
As a metabolite of the anesthetic Ropivacaine, (2S)-N-(2,6-Dimethylphenyl)-2-piperidinecarboxamide may play a role in the development of new anesthetic agents or the improvement of existing ones. Its presence in the metabolism of Ropivacaine suggests potential applications in the optimization of anesthetic drugs for better efficacy and safety.

Upstream product

• 98-98-6 2-Picolinic acid 
• 67-56-1 methanol 
• 39627-98-0 2-pyridine-carboxamide-N-(2,6-dimethylphenyl) 
• 87-62-7 2,6-dimethylaniline 
• 3105-95-1 pipecolinic acid 
• 98626-58-5 L-pipecolic acid chloride hydrochloride 
• 1537190-05-8 C₁₄H₂₀N₂O*C₁₆H₁₅NO₃ 
• 1537190-02-5 C₁₄H₂₀N₂O*C₁₆H₁₅NO₃ 
• 1537190-03-6 C₁₄H₂₀N₂O*C₁₆H₁₅NO₃ 
• 15883-20-2 2',6'-pipecoloxylidide 
• 178734-91-3 Acetic acid (S)-5-benzyloxycarbonylamino-5-(2,6-dimethyl-phenylcarbamoyl)-pentyl ester 
• 178734-92-4 [(S)-1-(2,6-Dimethyl-phenylcarbamoyl)-5-hydroxy-pentyl]-carbamic acid benzyl ester 
• 52192-32-2 (S)-6-acetoxy-2-(benzyloxycarbonyl)aminohexanoic acid 
• 2212-75-1 N₂-[(benzyloxy)carbonyl]-L-lysine 

Downstream Products

• 27262-39-1 (S)-dibenzoyl-2-pipecolinoxylidide-L-tartrate 
• 1364698-38-3 (R,S)-N-(2,6-dimethylphenyl)piperidinium-2-carboxamide bis-(trifluoromethylsulfonyl)imide 
• 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 
• 22801-44-1 (+)-Mepivacaine 
• 98626-59-6 (S)-1-ethyl-2',6'-pipecoloxylidide 
• 27262-47-1 levobupivacaine 
• 15883-20-2 2',6'-pipecoloxylidide 
• 175888-75-2 roivacaine 

Relevant articles and documents

A convenient and highly enantioselective synthesis of (S)-2-pipecolic acid: an efficient access to caine anesthetics

A novel and enantioselective synthesis of (S)-2-pipecolic acid (5) has been achieved from Oppolzer’s sultam (1) and ethyl N-(diphenylmethylene)glycinate (2) as readily available starting materials. The highly stereoselective alkylation of chiral glycine intermediate (3) with 1,4-dibromobutane afforded the key backbone of (S)-2-pipecolic acid (5) in one-step that was utilized into the preparation of the local anesthetics mepivacaine, ropivacaine and bupivacaine.

Preparation method of bupivacaine and intermediate (S)-2-piperidinecarboxylic acid thereof

The invention discloses bupivacaine and a preparation method of an intermediate (S)-2-piperidinecarboxylic acid of the bupivacaine; wherein the intermediate (S)-2-piperidinecarboxylic acid is prepared by taking (R)-4-benzyl-2-oxazolidinone as a chiral auxiliary agent through amidation, asymmetric alkylation, hydrolysis, cyclization and auxiliary group removal; wherein the prepared (S)-2-piperidinecarboxylic acid is used as a raw material to prepare the local anesthetic (S)-bupivacaine. The method utilizes cheap and easily available organic raw materials, and has the advantages of simple operation, mild reaction conditions, good stereoselectivity, high yield and the like.

Preparation and purification method of ropivacaine hydrochloride intermediate

The invention relates to a preparation and purification method of a ropivacaine hydrochloride intermediate. According to the method, single chiral intermediate (-)-(2S)-N-(2,6-dimethylphenyl)piperidine-2-carboxamide is prepared from single chiral raw mate

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.

Preparation method of ropivacaine hydrochloride

The invention discloses a preparation method of ropivacaine hydrochloride. The preparation method comprises steps as follows: (1) preparation of an intermediate (I), (2) preparation of an intermediate (II), (3) preparation of a crude product and (4) refin

Preparation method of bupivacaine hydrochloride

The invention discloses a preparation method of bupivacaine hydrochloride. The preparation method includes the steps of: 1) preparing N-(2,6-xylyl)-2-piperidineformamide; 2) preparing the bupivacaine hydrochloride. The reaction routes in the two steps are described in the specification. The method has high yield, high product quality and low operation cost, allows automation operation of equipment, has good stability, and can satisfy industrial demands.

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.

Effect of Partially Fluorinated N-Alkyl-Substituted Piperidine-2-carboxamides on Pharmacologically Relevant Properties

The modulation of pharmacologically relevant properties of N-alkyl-piperidine-2-carboxamides was studied by selective introduction of 1–3 fluorine atoms into the n-propyl and n-butyl side chains of the local anesthetics ropivacaine and levobupivacaine. The basicity modulation by nearby fluorine substituents is essentially additive and exhibits an exponential attenuation as a function of topological distance between fluorine and the basic center. The intrinsic lipophilicity of the neutral piperidine derivatives displays the characteristic response noted for partially fluorinated alkyl groups attached to neutral heteroaryl systems. However, basicity decrease by nearby fluorine substituents affects lipophilicities at neutral pH, so that all partially fluorinated derivatives are of similar or higher lipophilicity than their non-fluorinated parents. Aqueous solubilities were found to correlate inversely with lipophilicity with a significant contribution from crystal packing energies, as indicated by variations in melting point temperatures. All fluorinated derivatives were found to be somewhat more readily oxidized in human liver microsomes, the rates of degradation correlating with increasing lipophilicity. Because the piperidine-2-carboxamide core is chiral, pairs with enantiomeric N-alkyl groups are diastereomeric. While little response to such stereoisomerism was observed for basicity or lipophilicity, more pronounced variations were observed for melting point temperatures and oxidative degradation.

Synthesis method of bupivacaine

The invention belongs to a synthesis method of bupivacaine. The method comprises: adding 2 piperidinecarboxylicacid into aqueous alkali, dropwise adding Cbz and alkaline water, after finishing dropwise adding at normal temperature, reacting for 12 hours, after reaction, extracting with diethyl ether, washing a water layer to be weak-acid with 18% of diluted hydrochloric acid, extracting with the diethyl ether again, combining an diethyl ether layer, drying and filtering, and concentrating to obtain a dried product; adding the dried product into a DMF solvent, then adding a catalyst for reaction for 1 hour at normal temperature, then adding 2,6-dimethylaniline, reacting for 18hours at normal temperature, adding water and ethyl acetate for washing, taking an organic layer, drying and filtering, and concentrating to obtain a dried concentrated product; adding the dried concentrated product into a solvent, then adding a catalyst, pressurizing and introducing hydrogen, filtering after reaction and concentrating to obtain a dried product; adding the product in the above step into a solvent, dropwise adding bromo-n-butane at normal temperature, after dropwise adding, rising temperature to 80 DEG C for reacting for 12 hours, adding diluted hydrochloric acid, slowing cooling to normal temperature, and crystallizing, filtering and drying to obtain the product. The synthesis method has the advantages of higher yield, smaller pollution and low equipment requirement.

Topalgia treatment methods and compositions for treating

The invention relates to the compounds of formula (I) or its pharmaceutical acceptable salts, as well as polymorphs, solvates, enantiomers, stereoisomers and hydrates thereof. The pharmaceutical compositions comprising an effective amount of compounds of formula (I), and methods for the treatment of local pain may be formulated for oral, buccal, rectal, topical, transdermal, transmucosal, intravenous, parenteral administration, syrup, or injection. Such compositions may be used to treatment of infiltration, nerve block, epidural, intrathecal anesthesia, pain, severe pain, chronic pain, chemotherapy induced pain, neuropathic pain, post herpetic neuralgia, neuralgia, motor neurone disease, diabetic neuropathy, postheipetic neuralgia, injury, post-operative pain, osteoarthritis, rheumatoid arthritis, multiple sclerosis, spinal cord injury, migraine, HIV related neuropathic pain, cancer pain and Sower back pain.