17511-89-6

Basic information

• Product Name: (1-PHENYLCYCLOPENTYL)METHYLAMINE
• Synonyms: 1-(1-phenylcyclopentyl)methanamine(SALTDATA: FREE);(1-Phenylcyclopentyl)MethanaMine;1-(1-phenylcyclopentyl)methylamine;(1-phenylcyclopentyl)methanamine hydrochloride
• CAS NO: 17511-89-6
• Molecular Formula: C₁₂H₁₇N
• Molecular Weight: 175.27
• Mol File: 17511-89-6.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 276.4°Cat760mmHg
• Flash Point: 115.8°C
• Appearance: /
• Density: 0.995g/cm³
• Vapor Pressure: 0.00482mmHg at 25°C
• Refractive Index: 1.544
• CAS DataBase Reference: (1-PHENYLCYCLOPENTYL)METHYLAMINE(CAS DataBase Reference)
• NIST Chemistry Reference: (1-PHENYLCYCLOPENTYL)METHYLAMINE(17511-89-6)
• EPA Substance Registry System: (1-PHENYLCYCLOPENTYL)METHYLAMINE(17511-89-6)

Safety Data

• Hazardous Substances Data: 17511-89-6(Hazardous Substances Data)

Usage

General Description

(1-Phenylcyclopentyl)methylamine, also known as PCPMA, is a chemical compound with a complex structure. It consist of a cyclopentyl ring, which is a cyclic organic compound, attached to a phenyl group, and then further attached to a methylamine group, an organic compound with the formula CH3NH2. The presence of these groups makes this chemical polar and capable of forming hydrogen bonds. The properties and reactions of PCPMA will greatly depend on the presence and orientation of these different groups in the molecule. This chemical is not commonly found in many consumer products or natural sources but is primarily used in research and industrial settings.

InChI:InChI=1/C12H17N/c13-10-12(8-4-5-9-12)11-6-2-1-3-7-11/h1-3,6-7H,4-5,8-10,13H2

Synthetic route

1-phenyl-1-cyclopentanecarbonitrile (77-57-6) → (1-phenylcyclopentyl)methylamine (17511-89-6)

Conditions	Yield
With methanol; ammonia; nickel at 120℃; under 73550.8 Torr; Hydrogenation;
With lithium aluminium tetrahydride In tetrahydrofuran
With ammonia; hydrogen; nickel In methanol at 20 - 40℃; under 2585.7 Torr; for 40h;
With lithium aluminium tetrahydride In tetrahydrofuran at 20℃; for 2h;
With hydrogenchloride; hydrogen; 10% Pd/C In methanol; water; ethyl acetate

(1-phenylcyclopentyl)methylamine (17511-89-6) + 4-chlorobenzenesulfonyl chloride (98-60-2) → 4-Chloro-N-[[1-(phenyl)cyclopentyl]methyl]benzenesulfonamide (141336-27-8)

Conditions	Yield
With triethylamine In dichloromethane	92.3%

C16H12ClNO4 (1408396-53-1) + (1-phenylcyclopentyl)methylamine (17511-89-6) → N-[4-(1-phenylcyclopentylmethylcarbamoyl)phenyl]-1,4-benzodioxane-2-carboxamide (700858-24-8)

Conditions	Yield
With pyridine In 1,4-dioxane at 70 - 75℃;	78%

(1-phenylcyclopentyl)methylamine (17511-89-6) + ethyl 2-({[4-(4-methoxyphenyl)tetrahydro-2H-pyran-4-yl]methyl}amino)-2-oxoacetate → N-{[4-(4-methoxyphenyl)tetrahydro-2H-pyran-4-yl]methyl}-N′-[(1-phenylcyclopentyl)methyl]oxamide

Conditions	Yield
In ethanol for 8h; Reflux;	75%

(1-phenylcyclopentyl)methylamine (17511-89-6) + oxalic acid diethyl ester (95-92-1) → ethyl 2-oxo-2-[(1-phenylcyclopentylmethyl)amino]acetate (433704-86-0)

Conditions	Yield
In chloroform for 10h; Inert atmosphere; Reflux;	73%

ethyl 2-oxo-2-[(1-phenylcyclopentylmethyl)amino]acetate (433704-86-0) + (1-phenylcyclopentyl)methylamine (17511-89-6) → N,N'-bis(1-phenylcyclopentylmethyl)ethanediamide (445262-28-2)

Conditions	Yield
In ethanol for 8h; Reflux;	71%

C17H14ClNO3 (1408397-42-1) + (1-phenylcyclopentyl)methylamine (17511-89-6) → N-[4-(1-phenylcyclopentylmethylcarbamoyl)phenyl]isochroman-1-carboxamide (1395894-43-5)

Conditions	Yield
With pyridine In 1,4-dioxane at 70 - 75℃;	68%

ethyl 2-oxo-2-(o-methoxyphenylamino)acetate (7267-26-7) + (1-phenylcyclopentyl)methylamine (17511-89-6) → N-(2-methoxyphenyl)-N'-(1-phenylcyclopentylmethyl)ethanediamide (896162-12-2)

Conditions	Yield
at 65 - 70℃;	65%

ethyl 2-oxo-2-((3-(trifluoromethyl)phenyl)amino)acetate (17738-86-2) + (1-phenylcyclopentyl)methylamine (17511-89-6) → N-(1-phenylcyclopentylmethyl)-N'-(3-trifluoromethylphenyl)ethanediamide (896165-95-0)

Conditions	Yield
at 65 - 70℃;	61%

ethyl 2-((3-bromophenyl)amino)-2-oxoacetate (69066-31-5) + (1-phenylcyclopentyl)methylamine (17511-89-6) → N-(3-bromophenyl)-N'-(1-phenylcyclopentylmethyl)ethanediamide (896162-14-4)

Conditions	Yield
at 65 - 70℃;	60%

ethyl N-p-bromophenyloxamate (24451-15-8) + (1-phenylcyclopentyl)methylamine (17511-89-6) → N-(4-bromophenyl)-N'-(1-phenylcyclopentylmethyl)ethanediamide (891066-54-9)

Conditions	Yield
at 65 - 70℃;	59%

ethyl 2-((4-fluorophenyl)amino)-2-oxoacetate (69065-91-4) + (1-phenylcyclopentyl)methylamine (17511-89-6) → N-(4-fluorophenyl)-N'-(1-phenylcyclopentylmethyl)ethanediamide (896166-18-0)

Conditions	Yield
at 65 - 70℃;	57%

(1-phenylcyclopentyl)methylamine (17511-89-6) + 6',7'-dimethoxy-N-methyl-2'-(prop-2-enoyl)-2',3'-dihydro-1'H-spiro[cyclopentane-1,4'-isoquinoline]-1'-carboxamide → 6',7'-dimethoxy-N-methyl-2'-{3-[(1-phenylcyclopentyl)methylamino]propanoyl}-2',3'-dihydro-1'H-spiro[cyclopentane-1,4'-isoquinoline]-1'-carboxamide

Conditions	Yield
With hydrogenchloride In water at 55 - 60℃; for 35h;	48%

6-methoxy-5-(4-methyl-1H-imidazol-1-yl)pyrazine-2-carboxylic acid (1294003-44-3) + (1-phenylcyclopentyl)methylamine (17511-89-6) → 6-methoxy-5-(4-methyl-1H-imidazol-1-yl)-N-[(1-phenylcyclopentyl)methyl]pyrazine-2-carboxamide (1294002-18-8)

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 18h;	19%

oxirane (75-21-8) + (1-phenylcyclopentyl)methylamine (17511-89-6) → bis-(2-hydroxy-ethyl)-(1-phenyl-cyclopentylmethyl)-amine (101449-78-9)

formaldehyd (50-00-0) + (1-phenylcyclopentyl)methylamine (17511-89-6) → Dimethyl-(1-phenyl-cyclopentylmethyl)-amine

Conditions	Yield
With formic acid

diethyl sulfate (64-67-5) + (1-phenylcyclopentyl)methylamine (17511-89-6) → Ethyl-(1-phenyl-cyclopentylmethyl)-amine

mesityl isocyanate (2958-62-5) + (1-phenylcyclopentyl)methylamine (17511-89-6) → 1-(1-Phenyl-cyclopentylmethyl)-3-(2,4,6-trimethyl-phenyl)-urea

Conditions	Yield
In ethyl acetate for 20h; Ambient temperature;

1-(tert-butyl)-2-isocyanato-3-methylbenzene (13680-30-3) + (1-phenylcyclopentyl)methylamine (17511-89-6) → N-[2-(1,1-dimethylethyl)-6-methylphenyl]-N'-[(1-phenylcyclopentyl)methyl]urea

Conditions	Yield
In ethyl acetate for 20h; Ambient temperature;

2,6-diethylphenylisocyanate (20458-99-5) + (1-phenylcyclopentyl)methylamine (17511-89-6) → N-(2,6-diethylphenyl)-N'-[(1-phenylcyclopentyl)methyl]urea

Conditions	Yield
In ethyl acetate for 20h; Ambient temperature;

2,6-diisopropylphenyl isocyanate (28178-42-9) + (1-phenylcyclopentyl)methylamine (17511-89-6) → N-[2,6-bis(1-methylethyl)phenyl]-N'-[(1-phenylcyclopentyl)methyl]urea

Conditions	Yield
In ethyl acetate for 20h; Ambient temperature;

2,4-diflurophenylisocyanate (59025-55-7) + (1-phenylcyclopentyl)methylamine (17511-89-6) → N-(2,4-difluorophenyl)-N'-[(1-phenylcyclopentyl)methyl]urea

Conditions	Yield
In ethyl acetate for 20h; Ambient temperature;

(1-phenylcyclopentyl)methylamine (17511-89-6) + 1-ethyl-2-isocyanato-3-isopropylbenzene (102561-41-1) → N-[2-ethyl-6-(1-methylethyl)phenyl]-N'-[(1-phenylcyclopentyl)methyl]urea

Conditions	Yield
In ethyl acetate for 20h; Ambient temperature;

(1-phenylcyclopentyl)methylamine (17511-89-6) + 2,4,6-trifluorophenyl isocyanate (50528-80-8) → 1-(1-Phenyl-cyclopentylmethyl)-3-(2,4,6-trifluoro-phenyl)-urea

Conditions	Yield
In ethyl acetate for 20h; Ambient temperature;

(1-phenylcyclopentyl)methylamine (17511-89-6) + 2,4,6-trimethoxyphenyl isocyanate (134992-37-3) → 1-(1-Phenyl-cyclopentylmethyl)-3-(2,4,6-trimethoxy-phenyl)-urea

Conditions	Yield
In ethyl acetate for 20h; Ambient temperature;

(1-phenylcyclopentyl)methylamine (17511-89-6) + 2-isopropyl-6-methylphenyl isocyanate → N-[2-methyl-6-(1-methylethyl)phenyl]-N'-[(1-phenylcyclopentyl)methyl]urea

Conditions	Yield
In ethyl acetate for 20h; Ambient temperature;

(1-phenylcyclopentyl)methylamine (17511-89-6) + 2,4,6-trichlorophenyl isocyanate (2505-31-9) → 1-(1-Phenyl-cyclopentylmethyl)-3-(2,4,6-trichloro-phenyl)-urea

Conditions	Yield
In ethyl acetate for 20h; Ambient temperature;

(1-phenylcyclopentyl)methylamine (17511-89-6) + 2,6-dichlorophenylisocyanate (39920-37-1) → 1-(2,6-Dichloro-phenyl)-3-(1-phenyl-cyclopentylmethyl)-urea

Conditions	Yield
In ethyl acetate for 20h; Ambient temperature;

(1-phenylcyclopentyl)methylamine (17511-89-6) + 2,6-dimethylphenylisocyanate (28556-81-2) → N-(2,6-dimethylphenyl)-N'-[(1-PhenylcYclopentyl)methyl]urea

Conditions	Yield
In ethyl acetate for 20h; Ambient temperature;

4-(dimethylamino)benzoyl chloride (4755-50-4) + (1-phenylcyclopentyl)methylamine (17511-89-6) → 4-dimethylamino-N-(1-phenylcyclopentylmethyl)benzamide (190790-24-0)

Conditions	Yield
With triethylamine In tetrahydrofuran for 2h; Heating; Yield given;

Upstream product

• 77-57-6 1-phenyl-1-cyclopentanecarbonitrile 

Downstream Products

• 433704-86-0 ethyl 2-oxo-2-[(1-phenylcyclopentylmethyl)amino]acetate 
• 445264-76-6 N,N-bis(2-hydroxyethyl)-N'-(1-phenylcyclopentylmethyl)ethanediamide 
• 445264-75-5 N-(1-phenylcyclopentylmethyl)-N'-(pyridin-4-yl)ethanediamide 
• 713507-25-6 N-(1-phenylcyclopentylmethyl)-N'-(1,3,4-thiadiazol-2-yl)ethanediamide 
• 510718-08-8 2-(morpholin-4-yl)-2-oxo-N-(1-phenylcyclopentylmethyl)acetamide 
• 406189-87-5 2-oxo-2-(pyrrolidin-1-yl)-N-(1-phenylcyclopentylmethyl)acetamide 
• 445264-77-7 N,N-dibutyl-N'-(1-phenylcyclopentylmethyl)ethanediamide 
• 1450789-98-6 2-[methyl(1-phenylcyclopentyl)amino]ethanol hydrochloride 
• 433694-40-7 2-oxo-2-[(1-phenylcyclopentylmethyl)amino]acetic acid 
• 445262-28-2 N,N'-bis(1-phenylcyclopentylmethyl)ethanediamide 
• 445264-78-8 N-(furan-2-ylmethyl)-N'-(1-phenylcyclopentylmethyl)ethanediamide 
• 933206-07-6 N-[2-(morpholin-4-yl)ethyl]-N'-(1-phenylcyclopentylmethyl)ethanediamide 
• 896162-12-2 N-(2-methoxyphenyl)-N'-(1-phenylcyclopentylmethyl)ethanediamide 
• 896165-95-0 N-(1-phenylcyclopentylmethyl)-N'-(3-trifluoromethylphenyl)ethanediamide 

Relevant articles and documents

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The present invention relates to a compound having the general formula (V), optionally in the form of a pharmaceutically acceptable salt, solvate, polymorph, codrug, cocrystal, prodrug, tautomer, racemate, enantiomer, or diastereomer or mixture thereof, which are useful in treating, ameloriating or preventing a viral disease. Furthermore, specific combination therapies are disclosed.

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