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

Base Information

• Chemical Name: N-(2,6-dimethylphenyl)piperidine-2-carboxamide
• CAS No.: 15883-20-2
• Molecular Formula: C₁₄H₂₀N₂O
• Molecular Weight: 232.326
• Hs Code.: 2933399090
• European Community (EC) Number: 605-165-8
• UNII: NF8RN1V7VM
• DSSTox Substance ID: DTXSID90870436
• Nikkaji Number: J576.440H
• Wikidata: Q27284841
• Mol file: 15883-20-2.mol

Synonyms:2',6'-pipecoloxylidide;2',6'-pipecoloxylidide, (+)-isomer;2',6'-pipecoloxylidide, (-)-isomer;2',6'-pipecoloxylidide, (R)-isomer;2',6'-pipecoloxylidide, 14C-labeled;2',6'-pipecoloxylidide, monoacetate, (R)-isomer;desbutylbupivacaine;pipecolylxylidine-2',6'

Chemical Property of N-(2,6-dimethylphenyl)piperidine-2-carboxamide

Chemical Property:

• Appearance/Colour: Off-white to light yellow powder
• Melting Point: 114-117 ºC
• Boiling Point: 392.3 ºC at 760 mmHg
• PKA: 14.85±0.70(Predicted)
• Flash Point: 149 ºC
• PSA: 41.13000
• Density: 1.087 g/cm³
• LogP: 2.78580
• Storage Temp.: -20°C Freezer
• 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:

99.9% ^*data from raw suppliers

N-DesbutylBupivacaine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi,T
• Statements: 25
• Safety Statements: 45

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C(C(=CC=C1)C)NC(=O)C2CCCCN2
• Uses: A major metabolite of Bupivacaine N-(2,6-Dimethylphenyl)-1-methyl-1,2,5,6-tetrahydropyridine-2-carboxamide is a Bupivacaine (B689561) Impurity. Bupivacaine (B689561) is a sodium channel blocker, local anesthetic.

Technology Process of N-(2,6-dimethylphenyl)piperidine-2-carboxamide

There total 24 articles about N-(2,6-dimethylphenyl)piperidine-2-carboxamide 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:

(S)-2',6'-pipecoloxylidide

pipecolic-2-acid-2',6'-xylidide

bupivacaine hydrochloride

1-propyl-N-(2,6-dimethylphenyl)piperidine-2-carboxamide

Refernces

• 1、 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.
• 2、 Suveges, Nícolas S.,de Souza, Rodrigo O. M. A.,Gutmann, Bernhard,Kappe, C. Oliver. "Synthesis of Mepivacaine and Its Analogues by a Continuous-Flow Tandem Hydrogenation/Reductive Amination Strategy". . p. 6511 - 6517. Retrieved 2017/12/02.