(S)-N-(2-Methylphenyl)-2-(propylamino)propanamide

Base Information

• Chemical Name: (S)-N-(2-Methylphenyl)-2-(propylamino)propanamide
• CAS No.: 14289-31-7
• Molecular Formula: C₁₃H₂₀N₂O
• Molecular Weight: 220.315
• Nikkaji Number: J788.382J
• ChEMBL ID: CHEMBL1318078
• Mol file: 14289-31-7.mol

Synonyms:(S)-N-(2-Methylphenyl)-2-(propylamino)propanamide;14289-31-7;(S)-Prilocaine;(2S)-N-(2-methylphenyl)-2-(propylamino)propanamide;Propanamide, N-(2-methylphenyl)-2-(propylamino)-, (S)-;Lopac-P-9547;NCGC00016594-01;CAS-1786-81-8;SCHEMBL866149;CHEMBL1318078;NCGC00015860-01;PD132404

Chemical Property of (S)-N-(2-Methylphenyl)-2-(propylamino)propanamide

Chemical Property:

• Vapor Pressure: 2.05E-05mmHg at 25°C
• Boiling Point: 361.6°Cat760mmHg
• Flash Point: 134.3°C
• PSA: 0.00000
• Density: 1.029g/cm³
• LogP: 0.00000
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 5
• Exact Mass: 220.157563266
• Heavy Atom Count: 16
• Complexity: 218

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CCCNC(C)C(=O)NC1=CC=CC=C1C
• Isomeric SMILES: CCCN[C@@H](C)C(=O)NC1=CC=CC=C1C
• Uses: (S)-Prilocaine is a local anesthetic of the amino amide type. Prilocaine is often used in dentistry. Prilocaine is also often combined with lidocaine as a preparation for dermal anesthesia (lidocaine/prilocaine or EMLA), for treatment of conditions like paresthesia.

Technology Process of (S)-N-(2-Methylphenyl)-2-(propylamino)propanamide

There total 7 articles about (S)-N-(2-Methylphenyl)-2-(propylamino)propanamide 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: 97.0%

propylamine (107-10-8,42939-71-9) + 2-chloropropionyl chloride (7623-09-8) + o-toluidine (95-53-4) → prilocaine (721-50-6,14289-31-7)

Guidance literature:

2-chloropropionyl chloride; o-toluidine; With potassium carbonate; In acetone; at 0 - 30 ℃; for 5h;

propylamine; In acetone; at 70 ℃; for 14h;

Reference yield: 90.0%

propylamine (107-10-8,42939-71-9) + N-(2-methylphenyl)-2-chloropropanamide (19281-31-3) → prilocaine (721-50-6,14289-31-7)

Guidance literature:

With potassium carbonate; In acetone; Reflux;

Reference yield:

5-methyl-1-propyl-3-o-tolyl-imidazolidin-4-one; hydrochloride → prilocaine (721-50-6,14289-31-7)

Guidance literature:

In phosphate buffer; acetate buffer; at 60 ℃; pH=2.15 - 7.4; Kinetics;

DOI:10.1016/S0928-0987(03)00198-2

upstream raw materials:

propylamine

N-(2-methylphenyl)-2-chloropropanamide

2-chloropropionyl chloride

o-toluidine

Downstream raw materials:

C₄₂H₇₀O₃₅*C₁₃H₂₀N₂O

Refernces

• 1、 -. "Preparation method of prilocaine base". Paragraph 0017. . Retrieved 2016/10/31.