5327-45-7

Basic information

• Product Name: N-benzyloctadecanamide
• CAS NO: 5327-45-7
• Molecular Formula: C₂₅H₄₃NO
• Molecular Weight: 373.615
• Mol File: 5327-45-7.mol
• Article Data: 15

Chemical Properties

• Boiling Point: 525.3°C at 760 mmHg
• Flash Point: 326.3°C
• Density: 0.913g/cm³
• Vapor Pressure: 3.97E-11mmHg at 25°C
• Refractive Index: 1.489
• CAS DataBase Reference: N-benzyloctadecanamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-benzyloctadecanamide(5327-45-7)
• EPA Substance Registry System: N-benzyloctadecanamide(5327-45-7)

Safety Data

• Hazardous Substances Data: 5327-45-7(Hazardous Substances Data)

Usage

General Description

N-benzyloctadecanamide is a chemical compound that belongs to the class of amides and has the molecular formula C24H37NO. It consists of a long alkyl chain with a benzyl group attached to the nitrogen atom. N-benzyloctadecanamide is commonly used as an intermediate in the synthesis of various organic compounds, particularly in the production of pharmaceuticals and agrochemicals. It is also known for its potential biological activities, including anti-inflammatory and analgesic properties. N-benzyloctadecanamide has also been studied for its potential use in the treatment of skin disorders and as a local anesthetic. Overall, this compound has a wide range of applications in various fields, making it a versatile and important chemical in the industry.

Synthetic route

stearic acid (57-11-4) + benzyl azide (622-79-7) → N-benzyl-octadecanamide (5327-45-7)

Conditions	Yield
With 2,2'-dipyridyldiselenide; trimethylphosphane In toluene at 0 - 20℃; Staudinger-Vilarrasa reaction; Inert atmosphere;	94%

stearic acid (57-11-4) + benzylamine (100-46-9) → N-benzyl-octadecanamide (5327-45-7)

Conditions	Yield
With Bromotrichloromethane; 4-(diphenylphosphino)-benzyltrimethylammonium bromide; triethylamine In tetrahydrofuran; dichloromethane at 60℃; for 6h; Inert atmosphere;	93%
Stage #1: stearic acid With 1,1'-carbonyldiimidazole In dichloromethane at 20℃; for 2h; Stage #2: benzylamine With dmap In dichloromethane at 20℃; for 18h;	85%
With nano-Fe3O4-supported sulfonic acid In neat (no solvent) at 120℃; for 2h; Green chemistry;	76%

distearoyl diselenide (65212-12-6) + benzylamine (100-46-9) → N-benzyl-octadecanamide (5327-45-7)

Conditions	Yield
In benzene at 25℃; for 0.166667h;	88%

1-Pyrrol-1-yl-octadecan-1-one (86734-18-1) + benzylamine (100-46-9) → N-benzyl-octadecanamide (5327-45-7)

Conditions	Yield
In tetrahydrofuran for 16h; Heating;	87%
In tetrahydrofuran for 16h; Product distribution; Heating;	87%

Stearoyl chloride (112-76-5) + benzylamine (100-46-9) → N-benzyl-octadecanamide (5327-45-7)

Conditions	Yield
With benzene
With dmap In dichloromethane at 25℃; for 2h;

stearamide (124-26-5) → N-benzyl-octadecanamide (5327-45-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: 72 percent / Amberlyst A-21 resin / acetonitrile / 16 h / 55 °C 2: 87 percent / tetrahydrofuran / 16 h / Heating View Scheme

C36H50OSSi + benzylamine (100-46-9) → N-benzyl-octadecanamide (5327-45-7)

Conditions	Yield
In 5,5-dimethyl-1,3-cyclohexadiene at 60℃; Inert atmosphere;	120 mg

stearic acid (57-11-4) → N-benzyl-octadecanamide (5327-45-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: (2,3,4,5,6-pentafluorophenyl)ammonium triflate / 5,5-dimethyl-1,3-cyclohexadiene / 2 h / Inert atmosphere; Reflux 2: 5,5-dimethyl-1,3-cyclohexadiene / 60 °C / Inert atmosphere View Scheme
Multi-step reaction with 2 steps 1: thionyl chloride / dichloromethane / 2 h / 25 °C 2: dmap / dichloromethane / 2 h / 25 °C View Scheme

C25H50N2O2 + benzylamine (100-46-9) → N-benzyl-octadecanamide (5327-45-7)

Conditions	Yield
In water at 20℃; for 0.25h; Green chemistry;

N-benzyl-octadecanamide (5327-45-7) → stearic acid (57-11-4) + benzylamine (100-46-9)

Conditions	Yield
mit UV-Licht.Irradiation;

Upstream product

• 112-76-5 Stearoyl chloride 
• 100-46-9 benzylamine 
• 57-11-4 stearic acid 
• 622-79-7 benzyl azide 
• 124-26-5 stearamide 
• 86734-18-1 1-Pyrrol-1-yl-octadecan-1-one 
• 65212-12-6 distearoyl diselenide 

Downstream Products

• 57-11-4 stearic acid 
• 100-46-9 benzylamine 

Relevant articles and documents

Synthesis and biological screening of a library of macamides as TNF-α inhibitors

Thirty-five macamide analogues were synthesised by modifying the initial molecular structure. The resulting structures were confirmed using NMR and MS. Cytotoxicity and the anti-inflammatory activity of these synthetic macamides were evaluated in the THP-1 cell line. Preliminary biological evaluation indicated that most of these synthetic macamides did not present cytotoxicity (MTT assay) in the tested cell line with respect to the control (actinomycin D). Regarding the anti-inflammatory activity, several analogues had a greater potential for inhibition of TNF-α than natural macamides. Synthetic macamide 4a was the most active (IC50 = 0.009 ± 0.001 μM) compared to the C87 (control). Through looking at the link between the chemical structure and the activity, our study proves that changes made to natural macamides at the level of the alkyl chain, the benzyl position, the amide bond, and the addition of two methyl groups to the aromatic ring (meta position) lead us to obtaining new macamides with greater anti-inflammatory activity. This journal is

Amidation and esterification of carboxylic acids with amines and phenols by N,N′-diisopropylcarbodiimide: A new approach for amide and ester bond formation in water

The present study reports the successful synthesis of two important and abundant functional groups “ester and amide” by N,N′-diisopropylcarbodiimide (DIC) in water as a green solvent. A wide range of substrates could be employed with high functional group tolerance. The products were obtained in high yields after short reaction times. This method provides an efficient, economic, simple and very mild protocol for ester and amide bond formation in aqueous media. In addition, this work not only may lead to environmentally benign systems but also will provide a new aspect of organic chemistry in water.

Maca amide synthesis method and use thereof

The invention relates to a synthetic method of MACAmide. The method includes following steps: with a fatty acid and benzylamine or m-methoxybenzylamine as reaction raw materials, mixing the raw materials in a dichloromethane solution in which HOAt, EDC.HCl and DIPEA are dissolved; performing a reaction with stirring; washing a reaction product with water; and drying a substance being undissolved in water to obtain the MACAmide. The method is simple in processes and the raw materials are easy to obtain. Operation conditions of the method are easy to control. The reaction product can reach a purity of 95% without purification. The invention provides basis for industrialized synthesis of the MACAmide. In addition, the MACAmide has effects of enhancing male reproductive ability and treating male sexual dysfunction. The invention provides market prospects to application of the MACAmide.