(S)-N-(2,6-Dimethylphenyl)-2-piperidinecarboxamide

Base Information

• Chemical Name: (S)-N-(2,6-Dimethylphenyl)-2-piperidinecarboxamide
• CAS No.: 27262-40-4
• Molecular Formula: C14H20N2O
• Molecular Weight: 232.326
• European Community (EC) Number: 608-069-4
• UNII: 4A8HC6M4AL
• DSSTox Substance ID: DTXSID10181713
• Nikkaji Number: J958.393I
• Wikidata: Q27149622
• Mol file: 27262-40-4.mol

Synonyms:27262-40-4;(S)-N-(2,6-Dimethylphenyl)-2-piperidinecarboxamide;(S)-N-(2,6-Dimethylphenyl)piperidine-2-carboxamide;2-Piperidinecarboxamide, N-(2,6-dimethylphenyl)-, (2S)-;(2S)-N-(2,6-DIMETHYLPHENYL)-2-PIPERIDINECARBOXAMIDE;2',6'-Pipecoloxylidide, (+)-;Demethylmepivacaine, (+)-;Desbutylbupivacaine, (+)-;L-Pipecolic acid 2,6-xylidide;(2S)-N-(2,6-dimethylphenyl)piperidine-2-carboxamide;UNII-4A8HC6M4AL;4A8HC6M4AL;(S)-N-(2',6'-Dimethylphenyl)-2-piperidine carboxamide;(S)-N-(2',6'-Dimethylphenyl)piperidine-2-carboxylic amide;(S)-N-(2',6'-Dimethylphenl)-2-piperidine carboxamide;MFCD09038786;(2S)-N-(2,6-Dimethylphenyl)-2-piperidinecarboxamide);(2s)-pipecoloxylidide;N-Despropyl Ropivacaine;(+)-2',6'-pipecoloxylidide;(S)-2',6'-Pipecoloxylidide;SCHEMBL2616379;CHEBI:80578;DTXSID10181713;BCP22660;2/',6/'-Pipecoloxylidide, (+)-;AKOS015919828;AKOS030228178;AC-2122;AM62797;CS-W003585;DS-0592;FS-2874;(S)-N-(2 inverted exclamation marka,6 inverted exclamation marka-dimethylphenl)-2-Piperidine Carboxamide;D4347;Q-100343;Q27149622;ROPIVACAINE HYDROCHLORIDE MONOHYDRATE IMPURITY B [EP IMPURITY];(S)-N-(2 inverted exclamation mark ,6 inverted exclamation mark -dimethylphenyl)-piperidine-2- carboxylic amide

Chemical Property of (S)-N-(2,6-Dimethylphenyl)-2-piperidinecarboxamide

Chemical Property:

• Appearance/Colour: White powder
• Melting Point: 129-130 °C
• Boiling Point: 392.318 °C at 760 mmHg
• PKA: 14.85±0.70(Predicted)
• Flash Point: 148.954 °C
• PSA: 41.13000
• Density: 1.087g/cm³
• LogP: 2.78580
• Storage Temp.: Refrigerator
• Solubility.: DMSO, Methanol (Slightly), Water (Slightly, Heated and Sonicated)
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 232.157563266
• Heavy Atom Count: 17
• Complexity: 257

Purity/Quality:

99% Min ^*data from raw suppliers

N-Despropyl Ropivacaine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C(C(=CC=C1)C)NC(=O)C2CCCCN2
• Isomeric SMILES: CC1=C(C(=CC=C1)C)NC(=O)[C@@H]2CCCCN2
• Uses: N-Despropyl Ropivacaine (Ropivacaine EP Impurity B) is a major metabolite of Levobupivacaine (B689546) and the anesthetic Ropivacaine (R675000). A major metabolite of Levobupivacaine (B689546) and the anesthetic Ropivacaine (R675000).

Technology Process of (S)-N-(2,6-Dimethylphenyl)-2-piperidinecarboxamide

There total 51 articles about (S)-N-(2,6-Dimethylphenyl)-2-piperidinecarboxamide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 92.1%

[Cbz-piperidine-2-carboxylic acid (2,6-dimethyl-phenyl)-amide] → 2',6'-pipecoloxylidide (15883-20-2,27262-40-4,27262-43-7,78341-12-5)

Guidance literature:

With hydrogen; palladium on activated carbon; In methanol; for 0.5h;

Reference yield: 90.0%

(R)-2',6'-pipecoloxylidide → 2',6'-pipecoloxylidide (15883-20-2,27262-40-4,27262-43-7,78341-12-5)

Guidance literature:

With sodium hydroxide; In water; for 36h; Reflux;

Reference yield: 84.5%

2,6-dimethylaniline (87-62-7) + pipecolic Acid (4043-87-2,83680-83-5) → 2',6'-pipecoloxylidide (15883-20-2,27262-40-4,27262-43-7,78341-12-5)

Guidance literature:

pipecolic Acid; With hydrogenchloride; thionyl chloride; In N,N-dimethyl-formamide; toluene; at 45 - 55 ℃; for 3h; pH=2;

2,6-dimethylaniline; In N,N-dimethyl-formamide; toluene; for 2h; Solvent; Temperature; pH-value;

upstream raw materials:

1,4-dibromo-butane

2-amino-N-(2,6-dimethyl-phenyl)-malonamic acid ethyl ester

2-pyridine-carboxamide-N-(2,6-dimethylphenyl)

1-(tert-butoxycarbonyl)piperidine-2-carboxylic acid

Downstream raw materials:

levobupivacaine

(S)-dibenzoyl-2-pipecolinoxylidide-L-tartrate

(+)-Mepivacaine

(S)-1-ethyl-2',6'-pipecoloxylidide

Refernces

• 1、 Yang, Yuyan,Li, Hua,You, Zhonglin,Zhang, Xingxian. "A convenient and highly enantioselective synthesis of (S)-2-pipecolic acid: an efficient access to caine anesthetics". . p. 3084 - 3089. Retrieved 2021/08/12.
• 2、 Li, Wen,Ding, Lina,Liu, Hong-Min,You, Qidong. "Synthesis, biological evaluation, and molecular docking of ropivacaine analogs as local anesthetic agents". . p. 954 - 965. Retrieved 2017/11/29.