27262-47-1

Basic information

• Product Name: 1-Butyl-N-(2,6-dimethylphenyl)-piperidine-2-carboxamide
• Synonyms: 1-Butyl-N-(2,6-dimethylphenyl)-piperidine-2-carboxamide;Chirocaine;Levobupivacaine;(2S)-1-Butyl-N-(2,6-dimethylphenyl)piperidine-2α-carboxamide;2',6'-Pipecoloxylidide, 1-butyl-, L-(-)-;1-Butyl-N-(2,6-dimet;Levobupivacaine base;(2S)-1-Butyl-N-(2,6-diMethylphenyl)-2-piperidinecarboxaMide
• CAS NO: 27262-47-1
• Molecular Formula: C₁₈H₂₈N₂O
• Molecular Weight: 288.43
• EINECS: 1533716-785-6
• Product Categories: Chiral Reagents;Intermediates & Fine Chemicals;Pharmaceuticals;Inhibitors
• Mol File: 27262-47-1.mol
• Article Data: 22

Chemical Properties

• Melting Point: 136-137°C
• Boiling Point: 430.65°C (rough estimate)
• Flash Point: 209.9 °C
• Appearance: /
• Density: 1.0238 (rough estimate)
• Refractive Index: 1.5700 (estimate)
• Storage Temp.: Refrigerator
• PKA: 14.85±0.70(Predicted)
• CAS DataBase Reference: 1-Butyl-N-(2,6-dimethylphenyl)-piperidine-2-carboxamide(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Butyl-N-(2,6-dimethylphenyl)-piperidine-2-carboxamide(27262-47-1)
• EPA Substance Registry System: 1-Butyl-N-(2,6-dimethylphenyl)-piperidine-2-carboxamide(27262-47-1)

Safety Data

• Hazardous Substances Data: 27262-47-1(Hazardous Substances Data)

Usage

Description

1-Butyl-N-(2,6-dimethylphenyl)-piperidine-2-carboxamide is a complex organic compound with a molecular structure that features a piperidine ring, a butyl group, and a carboxamide functional group attached to a 2,6-dimethylphenyl group. 1-Butyl-N-(2,6-dimethylphenyl)-piperidine-2-carboxamide is characterized by its white solid appearance and is known for its potential applications in various industries.

Uses

Used in Pharmaceutical Industry:
1-Butyl-N-(2,6-dimethylphenyl)-piperidine-2-carboxamide is used as a local anesthetic for epidural and intrathecal anesthesia due to its ability to provide effective pain relief with lower risks of central nervous system (CNS) and cardiotoxicity compared to other anesthetic agents.
Used in Chemical Research:
As a white solid with unique chemical properties, 1-Butyl-N-(2,6-dimethylphenyl)-piperidine-2-carboxamide can be utilized in chemical research and development for the synthesis of new compounds or as an intermediate in the production of various pharmaceuticals and chemicals.
Used in Drug Metabolism Studies:
The compound's metabolic profile, including its pKa value and the enzymes responsible for its N-dealkylation and 3-hydroxylation, makes it a valuable subject for drug metabolism studies. Understanding its metabolic pathways can contribute to the development of safer and more effective drugs.

Originator

Chirocaine,Abbott Laboratories

Therapeutic Function

Local anesthetic

Pharmacology

This is the laevo (S–) enantiomer of bupivacaine, with similar properties to the racemic mixture, though it has slightly higher protein binding and clearance and hence a lower potential for cardiac and CNS toxicity. In practice, several other factors contribute to local anaesthetic toxicity, and the recommended maximum doses remain the same. Its formulation is expressed as percentage weight per unit volume of free base; racemic bupivacaine is expressed as percentage weight per unit volume of hydrochloride salt. Levobupivacaine therefore contains 13% more active molecules for a given dose.

InChI:InChI=1/C9H19N.C7H7NO.C2H6.ClH/c1-2-3-7-10-8-5-4-6-9-10;9-6-8-7-4-2-1-3-5-7;1-2;/h2-9H2,1H3;1-6H,(H,8,9);1-2H3;1H

Upstream product

• 123-72-8 butyraldehyde 
• 27262-40-4 (S)-2',6'-pipecoloxylidide 
• 3105-95-1 pipecolinic acid 
• 856838-98-7 (2S)-1-butylpiperidine-2-carboxylic acid 
• 87-62-7 2,6-dimethylaniline 
• 14252-80-3 bupivacaine hydrochloride 
• 542-69-8 1-iodo-butane 
• 109-65-9 1-bromo-butane 
• 178734-93-5 Toluene-4-sulfonic acid (S)-5-benzyloxycarbonylamino-5-(2,6-dimethyl-phenylcarbamoyl)-pentyl ester 
• 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 
• 14252-80-3 racemic bupivacaine 

Downstream Products

• 27262-45-9 (+)-Bupivacaine 

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.

Enantioseparation of racemic bupivacaine via ultrasonic-assisted diastereomeric crystallization using 12,14-dinitrodehydroabietic acid

12,14-Dinitrodehydroabietic acid (12,14-dinitroDHAA), a chiral acid obtained by the nitration of optical dehydroabietic acid (DHAA), was successfully employed as resolving agent. The resolution of racemic bupivacaine by ultrasonic-assisted diastereomeric crystallization in ethanol was investigated. The results indicated that ultrasonic-assist can well facilitate resolution of (R,S)-bupivacaine and a higher enantiomeric excess (ee) and yield was obtained for (S)-bupivacaine, and while without ultrasound, the ee value decreases by increasing the crystallization time. A Box-Behnken experimental design with four factors (amount of 12,14-dinitroDHAA, ethanol amount, ultrasonic power and crystallization temperature) combined with response surface methodology (RSM) was applied to explore resolution effects. A second-order polynomial equation was adequate to model the relationship between the ee (or yield) and the dependent variables. When maintaining a lower limit of 90% for the yield of (S)-bupivacaine, the optimal resolution conditions by RSM were 12,14-dinitroDHAA/bupivacaine molar ratio of 1.6, solvent/propranolol ratio of 16.5 mL/g, 63.2 W ultrasonic power and crystallization temperature of 0 °C, respectively. Under the optimal conditions, the experimental ee and yield of (S)-bupivacaine were 69.8% and 87.5%.