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

Chemical Properties

Off-White to Pale Yellow Solid

Uses

2-Amino-N-cyclohexyl-N-methylbenzylamine is an impurity of Bromhexine hydrochloride (B678600). Bromhexine hydrochloride impurity C.

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.