3312-60-5

Basic information

• Product Name: N-(3-AMINOPROPYL)CYCLOHEXYLAMINE
• Synonyms: 3-CYCLOHEXYLAMINOPROPYLAMINE;N-CYCLOHEXYL-1,3-PROPANEDIAMINE;N-CYCLOHEXYLPROPYLENE-1,3-DIAMINE;N-CYCLOHEXYL TRIMETHYLENE DIAMINE;N-(3-AMINOPROPYL)-CYCLOHEXANAMINE;N-(3-AMINOPROPYL)CYCLOHEXYLAMINE;RARECHEM AL BW 0425;1-(Cyclohexylamino)-3-aminopropane
• CAS NO: 3312-60-5
• Molecular Formula: C₉H₂₀N₂
• Molecular Weight: 156.27
• EINECS: 222-001-7
• Product Categories: Nitrogen Compounds;Organic Building Blocks;Polyamines;Building Blocks;Chemical Synthesis;Nitrogen Compounds;Organic Building Blocks
• Mol File: 3312-60-5.mol
• Article Data: 5

Chemical Properties

• Melting Point: −17-−15 °C(lit.)
• Boiling Point: 120-123 °C20 mm Hg(lit.)
• Flash Point: 214 °F
• Appearance: Pale yellow clear liquid
• Density: 0.917 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.0417mmHg at 25°C
• Refractive Index: n20/D 1.482(lit.)
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• Water Solubility: 5000g/L at 20℃
• Sensitive: Air Sensitive
• BRN: 741954
• CAS DataBase Reference: N-(3-AMINOPROPYL)CYCLOHEXYLAMINE(CAS DataBase Reference)
• NIST Chemistry Reference: N-(3-AMINOPROPYL)CYCLOHEXYLAMINE(3312-60-5)
• EPA Substance Registry System: N-(3-AMINOPROPYL)CYCLOHEXYLAMINE(3312-60-5)

Safety Data

• Hazard Codes: C,Xi
• Statements: 34
• Safety Statements: 26-27-28-36/37/39-45
• RIDADR: UN 2735 8/PG 2
• WGK Germany: 1
• TSCA: Yes
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 3312-60-5(Hazardous Substances Data)

Usage

Chemical Properties

colorless tolight yellow liquid

Uses

N-(3-Aminopropyl)cyclohexylamine is a competitive inhibitor of spermine and spermidine synthases.

InChI:InChI=1/C9H20N2/c10-7-4-8-11-9-5-2-1-3-6-9/h9,11H,1-8,10H2

Synthetic route

N-cyclohexyl-1,3-propanediamino-N,N'-bis(trimethylmethanesulfonamide) (198712-51-5) → N-(3-aminopropyl)cyclohexylamine (3312-60-5)

Conditions	Yield
With trifluorormethanesulfonic acid; methoxybenzene In dichloromethane at 20℃; for 2.5h; desulfonation;	67%

3-cyclohexylaminopropionitrile (702-03-4) → N-(3-aminopropyl)cyclohexylamine (3312-60-5)

Conditions	Yield
With ammonia; nickel at 120℃; under 128714 Torr; Hydrogenation;
With lithium aluminium tetrahydride
With hydrogen; nickel In methanol
With lithium aluminium tetrahydride In diethyl ether at 0℃;

3-cyclohexylaminopropionitrile (702-03-4) → bis-(N-cyclohexyl-3-aminopropyl)amine (80638-40-0) + N-(3-aminopropyl)cyclohexylamine (3312-60-5)

Conditions	Yield
With nickel Hydrogenation;

1-Cyclohexyl-1-(β-cyanethyl)-hydrazin (3956-37-4) → N-(3-aminopropyl)cyclohexylamine (3312-60-5)

Conditions	Yield
With hydrogen; nickel In methanol

cyclohexylamine (108-91-8) + acrylonitrile (107-13-1) → N-(3-aminopropyl)cyclohexylamine (3312-60-5)

Conditions	Yield
(i) EtOH, (ii) LiAlH4; Multistep reaction;

cyclohexylamine (108-91-8) + Co2(CO)8 → N-(3-aminopropyl)cyclohexylamine (3312-60-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: ethyl methyl ether / 78 °C 2: LiAlH4 / diethyl ether / 0 °C View Scheme

cyclohexylamine (108-91-8) → N-(3-aminopropyl)cyclohexylamine (3312-60-5)

Conditions	Yield
Multi-step reaction with 2 steps 2: Raney nickel; ethanolic ammonia / 120 °C / 128714 Torr / Hydrogenation View Scheme

cyclohexylhydrazine (6498-34-6) → N-(3-aminopropyl)cyclohexylamine (3312-60-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: ethanol 2: H2 / Raney-Ni / methanol View Scheme

cyclohexylamine (108-91-8) + sodium chloro sulfate → N-(3-aminopropyl)cyclohexylamine (3312-60-5)

Conditions	Yield
Multi-step reaction with 2 steps 2: LiAlH4 View Scheme

2-hydroxy-3-bromobenzaldehyde (1829-34-1) + N-(3-aminopropyl)cyclohexylamine (3312-60-5) → 2-bromo-6-[(3-cyclohexylaminopropylimino)methyl]phenol (1451054-32-2)

Conditions	Yield
In methanol at 20℃; for 1h;	100%
In methanol at 20℃;	91%
for 1h; Reflux;	83%
In ethanol for 1h; Reflux;	80%

5-benzoyl-3-(cyclopent-1-en-1-yl)-5-phenyl-1,5-dihydro-4H-pyrazol-4-one + N-(3-aminopropyl)cyclohexylamine (3312-60-5) → N-Cyclohexyl-N'-benzoyltrimethylen-1,3-diamin (52289-18-6)

Conditions	Yield
In dichloromethane at 20℃; for 0.5h; regioselective reaction;	99%

4-chloro-2-(2-furyl)-pyrimido[5,4-c]cinnoline (874903-63-6) + N-(3-aminopropyl)cyclohexylamine (3312-60-5) → N-cyclohexyl-N'-[2-(2-furyl)pyrimido[5,4-c]cinnolin-4-yl]propane-1,3-diamine

Conditions	Yield
In ethanol for 0.333333h; Heating;	95%

4-chloro-2-phenyl-pyrimido[5,4-c]cinnoline (874903-59-0) + N-(3-aminopropyl)cyclohexylamine (3312-60-5) → N-cyclohexyl-N'-[2-phenyl-pyrimido[5,4-c]cinnolin-4-yl]propane-1,3-diamine

Conditions	Yield
In ethanol for 0.333333h; Heating;	95%

4-Methyl-5,5-dioxo-1-p-tolyl-4,5-dihydro-1H-5λ6-thia-1,2,4-triaza-cyclopenta[a]naphthalene-3-carboxylic acid methyl ester (81761-75-3) + N-(3-aminopropyl)cyclohexylamine (3312-60-5) → 4-Methyl-5,5-dioxo-1-p-tolyl-4,5-dihydro-1H-5λ6-thia-1,2,4-triaza-cyclopenta[a]naphthalene-3-carboxylic acid (3-cyclohexylamino-propyl)-amide

Conditions	Yield
for 2h; Heating;	90%

N-(3-aminopropyl)cyclohexylamine (3312-60-5) + tetramethylammonium trifluoromethanethiolate → 1-cyclohexyltetrahydropyrimidine-2(1H)-thione (39148-52-2)

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 0.166667h;	89%

2-Nitrobenzenesulfonyl chloride (1694-92-4) + N-(3-aminopropyl)cyclohexylamine (3312-60-5) → N-(3-cyclohexylamino-propyl)-2-nitro-benzenesulfonamide

Conditions	Yield
With sodium hydrogencarbonate In tetrahydrofuran at 20℃; Substitution;	88%

(2,5-dioxopyrrolidin-1-yl)(E)-3-(2-fluorophenyl)-2-propenoate + N-(3-aminopropyl)cyclohexylamine (3312-60-5) → (E)-N-[3-(cyclohexylamino)propyl]-3-(2-fluorophenyl)-2-propenamide

Conditions	Yield
In tetrahydrofuran at 0 - 20℃; for 1h;	84%

2-amino-9-benzyl-6-chloro-9H-purine (6336-42-1) + N-(3-aminopropyl)cyclohexylamine (3312-60-5) → N6-[3-(cyclohexylamino)propyl]-9-phenylmethyl-9H-purine-2,6-diamine

Conditions	Yield
In ethanol at 60℃; for 24h;	82%

5-(4-chloro-benzenesulfonylamino)-1-(2-chloro-benzyl)-1H-imidazole-4-carboxylic acid ethyl ester + N-(3-aminopropyl)cyclohexylamine (3312-60-5) → 5-(4-chloro-benzenesulfonylamino)-1-(2-chloro-benzyl)-1H-imidazole-4-carboxylic acid (3-cyclohexylamino-propyl)-amide

Conditions	Yield
at 100℃; for 8h;	81%

N-acetyl-N-methoxyacetamide (128459-09-6) + N-(3-aminopropyl)cyclohexylamine (3312-60-5) → N-[3-(cyclohexylamino)propyl]-acetamide (128459-11-0)

Conditions	Yield
In water for 20.3h; Ambient temperature;	80%

3-Cyanobenzaldehyde (24964-64-5) + N-(3-aminopropyl)cyclohexylamine (3312-60-5) → C17H25N3 (917021-48-8)

Conditions	Yield
Stage #1: 3-Cyanobenzaldehyde; N-(3-aminopropyl)cyclohexylamine In methanol at 60℃; for 18h; Stage #2: With sodium tetrahydroborate In methanol at 20℃; for 0.5h;	80%

3-methoxy-2-hydroxybenzaldehyde (148-53-8) + N-(3-aminopropyl)cyclohexylamine (3312-60-5) → 2-[(3-cyclohexylaminopropylimino)methyl]-6-methoxyphenol (944934-09-2)

Conditions	Yield
In methanol for 3h; Reflux;	79%

2,4,6-trichloropyrimidine (3764-01-0) + N-(3-aminopropyl)cyclohexylamine (3312-60-5) → C24H42ClN5

Conditions	Yield
With triethylamine In tetrahydrofuran at 60℃;	75%

1-(4-Chloro-phenyl)-4-methyl-5,5-dioxo-4,5-dihydro-1H-5λ6-thia-1,2,4-triaza-cyclopenta[a]naphthalene-3-carboxylic acid methyl ester (81761-78-6) + N-(3-aminopropyl)cyclohexylamine (3312-60-5) → 1-(4-Chloro-phenyl)-4-methyl-5,5-dioxo-4,5-dihydro-1H-5λ6-thia-1,2,4-triaza-cyclopenta[a]naphthalene-3-carboxylic acid (3-cyclohexylamino-propyl)-amide

Conditions	Yield
for 2h; Heating;	74%

5-[bis-(4-chlorophenylsulfonyl)-amino]-1-(2,6-dichlorophenylmethyl)-1H-imidazole-4-carboxylic acid ethyl ester + N-(3-aminopropyl)cyclohexylamine (3312-60-5) → 5-(4-chloro-benzenesulfonylamino)-1-(2,6-dichloro-benzyl)-1H-imidazole-4-carboxylic acid (3-cyclohexylamino-propyl)-amide

Conditions	Yield
at 100℃; for 8h;	72%

cholic acid (81-25-4) + N-(3-aminopropyl)cyclohexylamine (3312-60-5) → N-[3-(cyclohexylamino)propyl]cholanamide

Conditions	Yield
Stage #1: cholic acid With triethylamine In tetrahydrofuran for 0.166667h; Cooling; Stage #2: With chloroformic acid ethyl ester In tetrahydrofuran at 20℃; for 0.166667h; Cooling; Stage #3: N-(3-aminopropyl)cyclohexylamine In tetrahydrofuran for 3h;	72%

di-tert-butyl dicarbonate (24424-99-5) + terephthalaldehyde mono(diethylacetal) (81172-89-6) + N-(3-aminopropyl)cyclohexylamine (3312-60-5) → C31H52N2O6

Conditions	Yield
Stage #1: terephthalaldehyde mono(diethylacetal); N-(3-aminopropyl)cyclohexylamine In methanol at 70℃; for 6h; Inert atmosphere; Molecular sieve; Stage #2: With sodium tetrahydroborate at 0 - 20℃; for 3h; Inert atmosphere; Stage #3: di-tert-butyl dicarbonate With sodium carbonate In water; tert-butyl alcohol at 20℃; for 12h; Inert atmosphere;	71%

4-cyanobenzaldehyde (105-07-7) + N-(3-aminopropyl)cyclohexylamine (3312-60-5) → C17H25N3 (917021-03-5)

Conditions	Yield
Stage #1: 4-cyanobenzaldehyde; N-(3-aminopropyl)cyclohexylamine In methanol at 60℃; for 6h; Stage #2: With sodium tetrahydroborate In methanol at 20℃; for 0.5h;	70%
Stage #1: 4-cyanobenzaldehyde; N-(3-aminopropyl)cyclohexylamine In methanol at 65℃; for 6h; Molecular sieve; Stage #2: With methanol; sodium tetrahydroborate at 20℃; Molecular sieve;

1-(2-Chloro-phenyl)-4-methyl-5,5-dioxo-4,5-dihydro-1H-5λ6-thia-1,2,4-triaza-cyclopenta[a]naphthalene-3-carboxylic acid methyl ester (81761-76-4) + N-(3-aminopropyl)cyclohexylamine (3312-60-5) → 1-(2-Chloro-phenyl)-4-methyl-5,5-dioxo-4,5-dihydro-1H-5λ6-thia-1,2,4-triaza-cyclopenta[a]naphthalene-3-carboxylic acid (3-cyclohexylamino-propyl)-amide

Conditions	Yield
for 2h; Heating;	69%

5-(4-chloro-benzenesulfonylamino)-1-phenethyl-1H-imidazole-4-carboxylic acid ethyl ester + N-(3-aminopropyl)cyclohexylamine (3312-60-5) → 5-(4-chloro-benzenesulfonylamino)-1-phenethyl-1H-imidazole-4-carboxylic acid (3-cyclohexylamino-propyl)-amide

Conditions	Yield
at 120℃; for 48h;	69%

2-amino-7-benzyl-6-chloro-7H-purine (93256-54-3) + N-(3-aminopropyl)cyclohexylamine (3312-60-5) → N6-[3-(cyclohexylamino)propyl]-7-phenylmethyl-7H-purine-2,6-diamine

Conditions	Yield
at 100℃; for 3h;	69%

4-chloro-2-(2-methoxyphenyl)-pyrimido[5,4-c]cinnoline (874903-61-4) + N-(3-aminopropyl)cyclohexylamine (3312-60-5) → N-cyclohexyl-N'-[2-(2-methoxyphenyl)-pyrimido[5,4-c]cinnolin-4-yl]propane-1,3-diamine

Conditions	Yield
In ethanol for 0.333333h; Heating;	66%

5-(4-chloro-benzenesulfonylamino)-1-(4-phenyl-butyl)-1H-imidazole-4-carboxylic acid ethyl ester + N-(3-aminopropyl)cyclohexylamine (3312-60-5) → 5-(4-chloro-benzenesulfonylamino)-1-(4-phenyl-butyl)-1H-imidazole-4-carboxylic acid (3-cyclohexylamino-propyl)-amide

Conditions	Yield
at 120℃; for 5h;	66%

5-(4-chloro-benzenesulfonylamino)-1-(3-chloro-benzyl)-1H-imidazole-4-carboxylic acid ethyl ester + N-(3-aminopropyl)cyclohexylamine (3312-60-5) → 5-(4-chloro-benzenesulfonylamino)-1-(3-chloro-benzyl)-1H-imidazole-4-carboxylic acid (3-cyclohexylamino-propyl)-amide

Conditions	Yield
at 120℃; for 3h;	65%

4-(tert-Butoxycarbonylaminomethyl)benzoic acid (33233-67-9) + N-(3-aminopropyl)cyclohexylamine (3312-60-5) → C22H35N3O3 (917021-35-3)

Conditions	Yield
With 4-methyl-morpholine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 25℃; for 18h;	65%

Upstream product

• 702-03-4 3-cyclohexylaminopropionitrile 
• 108-91-8 cyclohexylamine 
• 6498-34-6 cyclohexylhydrazine 
• 198712-51-5 N-cyclohexyl-1,3-propanediamino-N,N'-bis(trimethylmethanesulfonamide) 
• 107-13-1 acrylonitrile 
• 3956-37-4 1-Cyclohexyl-1-(β-cyanethyl)-hydrazin 

Downstream Products

• 47218-35-9 N¹-(7-chloroquinolin-4-yl)-N³-cyclohexylpropane-1,3-diamine 
• 69099-68-9 4H-thiochromeno[3,4-d]isoxazole-3-carboxylic acid 3-cyclohexylamino-propylamide 
• 30262-33-0 N-(2-Butyl-2-ethyl-5-methyl-hexa-3,4-dienyl)-N'-cyclohexyl-propane-1,3-diamine 
• 13860-67-8 3-Cyclohexylamino-propylguanidin 
• 63010-02-6 2-cyclohexyl-1,2,6-thiadiazinane-1,1-dioxide 
• 128459-11-0 N-[3-(cyclohexylamino)propyl]-acetamide 
• 81761-83-3 4-Methyl-5,5-dioxo-1-phenyl-4,5-dihydro-1H-5λ⁶-thia-1,2,4-triaza-cyclopenta[a]naphthalene-3-carboxylic acid (3-cyclohexylamino-propyl)-amide 
• 81761-98-0 1-(4-Chloro-phenyl)-4-methyl-5,5-dioxo-4,5-dihydro-1H-5λ⁶-thia-1,2,4-triaza-cyclopenta[a]naphthalene-3-carboxylic acid (3-cyclohexylamino-propyl)-amide 
• 917021-45-5 C₁₃H₂₂ClN₅ 
• 1029995-76-3 C₁₃H₂₄N₂O₂ 
• 1116571-51-7 5-(4-chlorophenylsulfonylamino)-N-(3-cyclohexylaminopropyl)-1-phenyl-1H-pyrazole-4-carboxamide 
• 944934-09-2 2-[(3-cyclohexylaminopropylimino)methyl]-6-methoxyphenol 

Relevant articles and documents

INHIBITORS OF BACTERIAL GLYCOSYL TRANSFERASES

Described herein are compounds of Formula (I'), Formula (IA), Formulae (I)-(VII), pharmaceutically acceptable salts, solvates, hydrates, polymorphs, co-crystals, tautomers, stereoisomers, isotopically labeled derivatives, and prodrug sthereof. The invention also provides pharmaceutical compositions of the compounds for human and veterinary use. Compounds of the present invention are useful for inhibiting bacterial growth and therefore are useful in treating and/or preventing bacterial infections. Methods of using the compounds for treating and/or preventing a bacterial infection in a subject are also described.

Tert-Butylsulfonyl (Bus), a New Protecting Group for Amines

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THE HYPOTENSIVE ACTIVITY OF N-CYCLOHEXYL AND N-METHYL DERIVATIVES OF

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