24358-84-7

Usage

Uses

Different sources of media describe the Uses of 24358-84-7 differently. You can refer to the following data:
1. Anesthetic.
2. (S)-Mepavacaine is a chemical often used as a local anesthetic.

InChI:InChI=1/C15H22N2O/c1-11-7-6-8-12(2)14(11)16-15(18)13-9-4-5-10-17(13)3/h6-8,13H,4-5,9-10H2,1-3H3,(H,16,18)/t13-/m0/s1

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 
• 50-00-0 formaldehyd 
• 27262-40-4 (S)-2',6'-pipecoloxylidide 
• 74-88-4 methyl iodide 
• 98626-58-5 L-pipecolic acid chloride hydrochloride 
• 3105-95-1 pipecolinic acid 
• 626-67-5 N-methylcyclohexylamine 
• 40397-98-6 2,5-dimethylphenyl isocyanate 
• 77-78-1 dimethyl sulfate 
• 111562-44-8 2-(2,6-dimethyl-phenylcarbamoyl)-1-methyl-pyridinium; iodide 

Relevant academic research and scientific papers

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.

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.

PROCESS FOR THE PREPARATION OF (S)-1-ALKYL-2',6'-PIPECOLOXYLIDIDE COMPOUND

The present invention relates to an improved process for the preparation of high chiral purity (S)-1-alkyl-2',6'-Pipecoloxylidide compound such as Ropivacaine, Levobupivacaine or salts thereof, which comprises crystallization of (S)-1-alkyl-2',6'- Pipecoloxylidide acid addition salt in a non-alcoholic and non-ketonic solvent.

Enantioselective total syntheses of ropivacaine and its analogues

An alternative asymmetric synthesis of ropivacaine and analogues employing the 'cation pool' strategy and host/guest supramolecular co-catalysis approach is presented. In this study, chiral auxiliaries, several soft nucleophiles as well as one-pot conditions for anodic oxidation, followed by nucleophilic addition, have been applied.

Radical fixation of functionalized carbon resources: α-sp 3C - H carbamoylation of tertiary amines with aryl isocyanates

A new carbamoylation of tertiary amines is reported. This rare C - H transformation features the direct generation of α-aminoalkyl radicals from tertiary amines, followed by the addition of the resultant nucleophilic radicals to isocyanates, enabling unique access to N,N-dialkylated amino acid derivatives. The authors put forward a mechanistic proposal that is based on the isolation of borinamides produced by capturing nitrogen radical intermediates with Et3B. The present transformation provides a novel one-step process for producing mepivacaine, a clinically important local anesthetic, from readily available materials.

Local anaesthetic salts of chondroitinsulfate compounds

Water-soluble local anaesthetic compounds having sustained effect are prepared by reacting a chondroitin derivative with a basic local anaesthetic compound.