Isomenthylamine

Base Information

• Chemical Name: Isomenthylamine
• CAS No.: 4894-99-9
• Molecular Formula: C₁₀H₂₁N
• Molecular Weight: 155.283
• Mol file: 4894-99-9.mol

Synonyms:Isomenthylamine

Chemical Property of Isomenthylamine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• General Description: Isomenthylamine is one of the optically active N-alkyl derivatives produced during the reductive amination of l-menthol with aliphatic nitriles, specifically accounting for 17% of the isomeric mixture, which also includes menthylamine (54%), neomenthylamine (24%), and neoisomenthylamine (5%). Its formation is attributed to the stereochemical outcomes of the reaction under the described catalytic conditions.

Technology Process of Isomenthylamine

There total 9 articles about Isomenthylamine 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: 98.0%

DL-neomenthol (490-99-3,491-01-0,491-02-1,1490-04-6,2216-51-5,2216-52-6,3623-51-6,3623-52-7,3623-53-8,15356-60-2,15356-70-4,20747-49-3,20752-33-4,20752-34-5,23283-97-8,64282-88-8,89-78-1) → rac-menthylamine (2216-54-8,4894-99-9,7231-40-5,16934-77-3,20706-69-8,20706-70-1,21411-81-4,23399-21-5,51743-63-6,66609-74-3,85549-06-0,787534-09-2)

Guidance literature:

DL-neomenthol; With 1-methyl-1H-imidazole; methanesulfonyl chloride; triethylamine; In toluene; at 20 ℃; for 2h;

With sodium azide; In N,N-dimethyl-formamide; at 40 ℃; for 48h;

With hydrogen; nickel; In tetrahydrofuran; at 20 ℃; for 72h;

DOI:10.1002/ejoc.201301566

Reference yield: 98.0%

2‐azido‐1‐isopropyl‐4‐methylcyclohexane (898543-45-8,898543-46-9) → rac-menthylamine (2216-54-8,4894-99-9,7231-40-5,16934-77-3,20706-69-8,20706-70-1,21411-81-4,23399-21-5,51743-63-6,66609-74-3,85549-06-0,787534-09-2)

Guidance literature:

With hydrogen; In tetrahydrofuran; at 20 ℃; for 72h;

DOI:10.1055/s-0030-1258295

Reference yield:

→ rac-menthylamine (2216-54-8,4894-99-9,7231-40-5,16934-77-3,20706-69-8,20706-70-1,21411-81-4,23399-21-5,51743-63-6,66609-74-3,85549-06-0,787534-09-2)

Guidance literature:

With ethanol; sodium;

upstream raw materials:

ethanol

(+/-)-isomenthone oxime

2‐azido‐1‐isopropyl‐4‐methylcyclohexane

DL-neomenthol

Downstream raw materials:

(+)-(1R,3S,4S)-neomenthylamine

(+)-neomenthylamine

2-isopropyl-5-methyl-cyclohexylamine

(1S,3S,4R)-menthylamine

Refernces

REDUCTIVE AMINATION OF l-MENTHOL BY ALIPHATIC NITRILES

10.1007/BF00568510

The research investigates the reductive amination of l-menthol using aliphatic nitriles, aiming to understand the stereochemical composition of the products and propose a mechanism for the reaction. The study utilized a copper-alumina catalyst modified with lithium hydroxide and conducted the reaction under specific conditions of temperature, pressure, and space velocity. The chemicals involved included l-menthol, aliphatic nitriles such as acetonitrile, acrylonitrile, and butyronitrile, and a catalyst composed of 15% copper and 6% lithium hydroxide on alumina. The results showed that the reaction produced a mixture of isomeric optically active N-alkyl derivatives of menthylamine, neomenthylamine, isomenthylamine, and neoisomenthylamine in a ratio of 54:24:17:5.