57365-08-9

Basic information

• Product Name: 2-AMINO-N-CYCLOHEXYL-N-METHYLBENZENE METHAMINE HCL
• Synonyms: LABOTEST-BB LT00159416;2-AMINO-N-CYCLOHEXYL-N-METHYLBENZENE METHAMINE HCL;2-AMINO-N-CYCLOHEXYL-N-METHYLBENZYLAMINE;2-Amino-N-cyclohexyl-N-methylbenzene methamine hydrochloride;N 2 - Amino Benzyl Cyclohexyl Methylamine;Einecs 260-701-4;2-[(CyclohexylMethylaMino)Methyl]phenylaMine;N-(2-AMinobenzyl)-N-MethylcyclohexanaMine
• CAS NO: 57365-08-9
• Molecular Formula: C₁₄H₂₂N₂
• Molecular Weight: 218.34
• EINECS: 260-701-4
• Product Categories: Nitrogen Compounds;Organic Building Blocks;Polyamines;Amines;Aromatics;Impurities;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 57365-08-9.mol
• Article Data: 1

Chemical Properties

• Melting Point: 44-47 °C(lit.)
• Boiling Point: 343.8 °C at 760 mmHg
• Flash Point: 147.4 °C
• Appearance: /
• Density: 1.02 g/cm³
• Vapor Pressure: 6.89E-05mmHg at 25°C
• Refractive Index: 1.563
• Storage Temp.: Refrigerator, Under Inert Atmosphere
• Solubility: Acetonitrile (Slightly), DMSO (Slightly), Methanol (Slightly)
• PKA: 8.78±0.20(Predicted)
• CAS DataBase Reference: 2-AMINO-N-CYCLOHEXYL-N-METHYLBENZENE METHAMINE HCL(CAS DataBase Reference)
• NIST Chemistry Reference: 2-AMINO-N-CYCLOHEXYL-N-METHYLBENZENE METHAMINE HCL(57365-08-9)
• EPA Substance Registry System: 2-AMINO-N-CYCLOHEXYL-N-METHYLBENZENE METHAMINE HCL(57365-08-9)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26
• WGK Germany: 3
• Hazardous Substances Data: 57365-08-9(Hazardous Substances Data)

Usage

Description

2-AMINO-N-CYCLOHEXYL-N-METHYLBENZENE METHAMINE HCL, also known as Bromhexine hydrochloride impurity C, is an off-white to pale yellow solid. It is an impurity found in Bromhexine hydrochloride (B678600), a medication used for respiratory conditions.

Uses

Used in Pharmaceutical Industry:
2-AMINO-N-CYCLOHEXYL-N-METHYLBENZENE METHAMINE HCL is used as an impurity in the production of Bromhexine hydrochloride for the pharmaceutical industry. Its presence is important for the quality control and safety of the final drug product, as impurities can affect the efficacy and safety of medications. The management and control of impurities like Bromhexine hydrochloride impurity C are crucial in ensuring the overall quality and performance of the drug.

InChI:InChI=1/C14H22N2/c1-16(13-8-3-2-4-9-13)11-12-7-5-6-10-14(12)15/h5-7,10,13H,2-4,8-9,11,15H2,1H3

Synthetic route

N-methylcyclohexylamine (100-60-7) + ortho-(chloromethyl)-aniline (114059-99-3) → N-(2-aminobenzyl)-N-cyclohexyl-N-methylamine (57365-08-9)

Conditions	Yield
In ethanol at 20℃; for 1.5h; Time; Solvent; Reflux;	85%

2-hydroxy-5-methoxybenzaldehyde (672-13-9) + N-(2-aminobenzyl)-N-cyclohexyl-N-methylamine (57365-08-9) → C22H28N2O2

Conditions	Yield
In toluene Dean-Stark; Reflux;	96%
In toluene Reflux;

N-(2-aminobenzyl)-N-cyclohexyl-N-methylamine (57365-08-9) + 5-bromosalicyclaldehyde (1761-61-1) → C21H25BrN2O

Conditions	Yield
In toluene Dean-Stark; Reflux;	96%

N-(2-aminobenzyl)-N-cyclohexyl-N-methylamine (57365-08-9) + 5-chlorosalicyclaldehyde (635-93-8) → C21H25ClN2O

Conditions	Yield
In toluene Dean-Stark; Reflux;	95%

N-(2-aminobenzyl)-N-cyclohexyl-N-methylamine (57365-08-9) + salicylaldehyde (90-02-8) → C21H26N2O

Conditions	Yield
In toluene for 24h; Dean-Stark; Reflux;	95%
In toluene Reflux;

2-Hydroxy-4-methoxybenzaldehyde (673-22-3) + N-(2-aminobenzyl)-N-cyclohexyl-N-methylamine (57365-08-9) → C22H28N2O2

Conditions	Yield
In toluene Dean-Stark; Reflux;	95%
In toluene Reflux;

3,5-di-tert-butyl-2-hydroxybenzaldehyde (37942-07-7) + N-(2-aminobenzyl)-N-cyclohexyl-N-methylamine (57365-08-9) → C29H42N2O

Conditions	Yield
In toluene for 48h; Reflux; Dean-Stark;	95%

N-(2-aminobenzyl)-N-cyclohexyl-N-methylamine (57365-08-9) + 3-methoxy-2-hydroxybenzaldehyde (148-53-8) → C22H28N2O2

Conditions	Yield
In toluene for 24h; Reflux; Dean-Stark;	95%

4-(Diethylamino)salicylaldehyde (17754-90-4) + N-(2-aminobenzyl)-N-cyclohexyl-N-methylamine (57365-08-9) → C25H35N3O

Conditions	Yield
In toluene for 168h; Dean-Stark; Reflux;	92%

N-(2-aminobenzyl)-N-cyclohexyl-N-methylamine (57365-08-9) + [4-methyl-3-(4-pyridin-3-yl-pyrimidin-2-ylamino)-phenyl]-carbamic acid 4-nitro-phenyl ester; hydrochloride → 1-{2-[(cyclohexyl-methyl-amino)-methyl]-phenyl}-3-[4-methyl-3-(4-pyridin-3-yl-pyrimidin-2-ylamino)-phenyl]-urea

Conditions	Yield
With triethylamine In N,N-dimethyl-formamide

2-hydroxy-5-methoxybenzaldehyde (672-13-9) + N-(2-aminobenzyl)-N-cyclohexyl-N-methylamine (57365-08-9) → C44H54N4Na2O4

Conditions	Yield
Multi-step reaction with 2 steps 1: toluene / Dean-Stark; Reflux 2: tetrahydrofuran / -95 - 20 °C View Scheme

N-(2-aminobenzyl)-N-cyclohexyl-N-methylamine (57365-08-9) + 5-chlorosalicyclaldehyde (635-93-8) → C42H48Cl2N4Na2O2

Conditions	Yield
Multi-step reaction with 2 steps 1: toluene / Dean-Stark; Reflux 2: tetrahydrofuran / -95 - 20 °C View Scheme

N-(2-aminobenzyl)-N-cyclohexyl-N-methylamine (57365-08-9) + salicylaldehyde (90-02-8) → C42H50N4Na2O2

Conditions	Yield
Multi-step reaction with 2 steps 1: toluene / 24 h / Dean-Stark; Reflux 2: tetrahydrofuran / 15 h / -95 - 20 °C View Scheme

4-(Diethylamino)salicylaldehyde (17754-90-4) + N-(2-aminobenzyl)-N-cyclohexyl-N-methylamine (57365-08-9) → C50H68N6Na2O2

Conditions	Yield
Multi-step reaction with 2 steps 1: toluene / 168 h / Dean-Stark; Reflux 2: tetrahydrofuran / -95 - 20 °C View Scheme

2-Hydroxy-4-methoxybenzaldehyde (673-22-3) + N-(2-aminobenzyl)-N-cyclohexyl-N-methylamine (57365-08-9) → C44H54N4Na2O4

Conditions	Yield
Multi-step reaction with 2 steps 1: toluene / Dean-Stark; Reflux 2: tetrahydrofuran / -95 - 20 °C View Scheme

N-(2-aminobenzyl)-N-cyclohexyl-N-methylamine (57365-08-9) + salicylaldehyde (90-02-8) → C23H30N2OZn

Conditions	Yield
Multi-step reaction with 2 steps 1: toluene / Reflux 2: toluene / 12 h / 0 °C / Inert atmosphere View Scheme

2-Hydroxy-4-methoxybenzaldehyde (673-22-3) + N-(2-aminobenzyl)-N-cyclohexyl-N-methylamine (57365-08-9) → C24H32N2O2Zn

Conditions	Yield
Multi-step reaction with 2 steps 1: toluene / Reflux 2: toluene / 12 h / 0 °C / Inert atmosphere View Scheme

2-hydroxy-5-methoxybenzaldehyde (672-13-9) + N-(2-aminobenzyl)-N-cyclohexyl-N-methylamine (57365-08-9) → C24H32N2O2Zn

Conditions	Yield
Multi-step reaction with 2 steps 1: toluene / Reflux 2: toluene / 12 h / 0 °C / Inert atmosphere View Scheme

N-(2-aminobenzyl)-N-cyclohexyl-N-methylamine (57365-08-9) + 3-methoxy-2-hydroxybenzaldehyde (148-53-8) → C24H32N2O2Zn

Conditions	Yield
Multi-step reaction with 2 steps 1: toluene / 24 h / Reflux; Dean-Stark 2: toluene / 12 h / 0 °C / Inert atmosphere View Scheme

N-(2-aminobenzyl)-N-cyclohexyl-N-methylamine (57365-08-9) + 8-(methylamino)-2-oxo-1,2-dihydroquinoline-3-carboxylic acid → N-(2-[[cyclohexyl(methyl)amino]methyl]phenyl)-8-(methylamino)-2-oxo-1,2-dihydroquinoline-3-carboxamide

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide at 20℃; for 7h;	15 mg

Upstream product

• 100-60-7 N-methylcyclohexylamine 
• 114059-99-3 ortho-(chloromethyl)-aniline 

Relevant articles and documents

Preparation method of bromhexine hydrochloride impurity C

The invention relates to the field of chemical pharmacy, in particular to a preparation method of bromhexine hydrochloride impurity C: N-methyl-N-cyclohexyl-2-aminobenzene methylamine. The method hasobvious advantages in the aspects of rapidness, high efficiency and economy. The prepared high-purity N-methyl-N-cyclohexyl-2-aminobenzene methylamine has important significance for the quality research of bromhexine hydrochloride. The preparation method comprises the following steps: (1) adding o-aminobenzyl alcohol into thionyl chloride in batches, reacting at room temperature, evaporating a solvent to dryness after the reaction is finished, adding a pulping solvent, pulping and filtering to obtain a compound 1; (2) adding the compound 1 into N-methylcyclohexylamine in batches, reacting at room temperature, after the reaction is finished, adding a solvent, refluxing, decolorizing with activated carbon, filtering, and evaporating filtrate to dryness to obtain an impurity C.