5906-35-4

Basic information

• Product Name: 1-AMINOHOMOPIPERIDINE
• Synonyms: 1,1-Hexamethylenehydrazine;1-Aminohexahydro-1H-azepine;1-Aminohexamethyleneimine;1-Aminoperhydroazepine;1-Azepanamine;1H-Azepine, 1-aminohexahydro-;1H-Azepine, hexahydro-1-amino-;Aminohexamethyleneimine
• CAS NO: 5906-35-4
• Molecular Formula: C₆H₁₄N₂
• Molecular Weight: 114.19
• EINECS: 227-609-6
• Product Categories: Heterocyclic Compounds
• Mol File: 5906-35-4.mol
• Article Data: 4

Chemical Properties

• Melting Point: 86.0-86.5 °C
• Boiling Point: 165 °C(lit.)
• Flash Point: 133 °F
• Appearance: /
• Density: 0.984 g/mL at 25 °C(lit.)
• Vapor Pressure: 1.86mmHg at 25°C
• Refractive Index: n20/D 1.485(lit.)
• Storage Temp.: 2-8°C
• PKA: 8.19±0.20(Predicted)
• CAS DataBase Reference: 1-AMINOHOMOPIPERIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-AMINOHOMOPIPERIDINE(5906-35-4)
• EPA Substance Registry System: 1-AMINOHOMOPIPERIDINE(5906-35-4)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• RIDADR: UN 1993 3/PG 3
• WGK Germany: 3
• RTECS: CM3165000
• HazardClass: 3.2
• PackingGroup: III
• Hazardous Substances Data: 5906-35-4(Hazardous Substances Data)

Usage

Chemical Properties

Liquid. Soluble in water and most organic solvents. Combustible.

Uses

N-Aminohexamethylenimine is a sesquiterpene lactones with anti-hepatitis C virus activity.

InChI:InChI=1/C6H14N2/c7-8-5-3-1-2-4-6-8/h1-7H2

Synthetic route

sodium hydroxide (1310-73-2) + (R)-3-aminoazepan-2-one hydrochloride → 1-azepanylamine (5906-35-4)

Conditions	Yield
With hydrogenchloride In tetrahydrofuran; water; ethyl acetate	90%

1 ,6-dibromohexane (629-03-8) + hydrazine hydrate (7803-57-8) → 1-azepanylamine (5906-35-4)

Conditions	Yield
In methanol for 25.5h; Reflux;	45%

hexamethylene imine (111-49-9) → 1-azepanylamine (5906-35-4)

(CH2)6NNH2*BH3 (21223-22-3) + water (7732-18-5) → hydrogen (1333-74-0) + boric acid (11113-50-1) + 1-azepanylamine (5906-35-4)

Conditions	Yield
In water
In water

1-azepanylamine (5906-35-4) + diethyl 2-ethoxymethylenemalonate (87-13-8) → (hexahydro-1H azepinyl-1 amino)-3 ethoxycarbonyl-2 propenoate d'ethyle (94621-04-2)

Conditions	Yield
In methanol for 1h; Ambient temperature;	98%

1,1,1,2,2,2-hexamethyldisilane (1450-14-2) + 1-azepanylamine (5906-35-4) → 1-homopiperidine (121667-16-1)

Conditions	Yield
With potassium hydride In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide for 24h; Ambient temperature;	97%

2-ethoxycarbonyl-1-cyclopentanone (611-10-9) + 1-azepanylamine (5906-35-4) → (hexahydro-1H-azepinyl-1 amino)-2 ethoxycarbonyl-1 cyclopentene

Conditions	Yield
With sodium sulfite In diethyl ether for 24h; Ambient temperature;	95%

5-nitrofurane-2-carboxaldehyde (698-63-5) + 1-azepanylamine (5906-35-4) → 1-(5-nitrofurfurylideneamino)azepane

Conditions	Yield
for 0.25h; Heating;	94%

2-chloro-6-methylphenyl isocyanate (40398-01-4) + 1-azepanylamine (5906-35-4) → 1-Azepan-1-yl-3-(2-chloro-6-methyl-phenyl)-urea

Conditions	Yield
In benzene Heating;	92%

1-azepanylamine (5906-35-4) + 2,6-dimethylphenylisocyanate (28556-81-2) → 1-Azepan-1-yl-3-(2,6-dimethyl-phenyl)-urea

Conditions	Yield
In benzene Heating;	92%

1-azepanylamine (5906-35-4) + 2-Fluorobenzoyl chloride (393-52-2) → 2-fluoro-N-(1-azepanyl)benzamide

Conditions	Yield
With triethylamine In diethyl ether for 2h; Ambient temperature;	92%

2-chloro-5-nitrobenzoylchloride (25784-91-2) + 1-azepanylamine (5906-35-4) → 2-chloro-5-nitro-N-(1-azepanyl)benzamide (150929-61-6)

Conditions	Yield
With triethylamine In diethyl ether for 2h; Ambient temperature;	90%

1-azepanylamine (5906-35-4) + 2-tolyl isocyanate (614-68-6) → 1-Azepan-1-yl-3-o-tolyl-urea

Conditions	Yield
In benzene Heating;	88%

N‑methyl‑2‑oxo‑2‑phenylacetamide (83490-71-5) + 1-azepanylamine (5906-35-4) → 2-[(E)-Azepan-1-ylimino]-N-methyl-2-phenyl-acetamide

Conditions	Yield
With acetic acid In ethanol for 24h; Heating;	88%

1-azepanylamine (5906-35-4) + 5-(4-bromophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carboxylic chloride (183232-64-6) → 5-(4-bromo-phenyl)-1-(2,4-dichloro-phenyl)-4-methyl-1H-pyrazole-3-carboxylic acid azepan-1-ylamide

Conditions	Yield
With triethylamine In dichloromethane for 3h; Ambient temperature;	88%

3-pyridinecarboxaldehyde (500-22-1) + 1-azepanylamine (5906-35-4) → Azepan-1-yl-[1-pyridin-3-yl-meth-(E)-ylidene]-amine (125142-75-8)

Conditions	Yield
In ethanol for 0.5h; heating on a steam bath;	87%

1-azepanylamine (5906-35-4) + chlorobenzene (108-90-7) → C12H18N2

Conditions	Yield
With potassium tert-butylate; tris(dibenzylideneacetone)dipalladium (0) In 1,4-dioxane at 120℃; for 5h;	87%

2-oxo-propionic acid ethyl ester (617-35-6) + 1-azepanylamine (5906-35-4) → ethyl 2-(azepan-1-ylimino)propanoate (1159014-98-8)

Conditions	Yield
In ethanol at 0 - 20℃;	87%
In ethanol at 20℃; for 4h;

1-azepanylamine (5906-35-4) + benzil (134-81-6) → 2-[(Z)-Azepan-1-ylimino]-1,2-diphenyl-ethanone (109541-25-5)

Conditions	Yield
With potassium hydroxide In ethanol for 24h; Ambient temperature;	86%
With acetic acid In ethanol for 20h; Ambient temperature;	58%

1-azepanylamine (5906-35-4) + 3-chlorotrifluoromethylbenzene (98-15-7) → C13H17F3N2

Conditions	Yield
With potassium tert-butylate; tris(dibenzylideneacetone)dipalladium (0) In 1,4-dioxane at 120℃; for 4.5h;	86%

2-methylchlorobenzene (95-49-8) + 1-azepanylamine (5906-35-4) → C13H20N2

Conditions	Yield
With potassium tert-butylate; tris(dibenzylideneacetone)dipalladium (0) In 1,4-dioxane at 120℃; for 5h;	85%

1-azepanylamine (5906-35-4) + 2-(4-chlorophenyl)-2-phenyl-1,3-dioxolane (374589-65-8) → C21H26N2O2

Conditions	Yield
With potassium tert-butylate; tris(dibenzylideneacetone)dipalladium (0) In 1,4-dioxane at 120℃; for 6h;	85%

1-azepanylamine (5906-35-4) → N-methyleneazepan-1-amine (54253-55-3)

Conditions	Yield
	85%

L-arabinose (5328-37-0) + 1-azepanylamine (5906-35-4) → (2S,3R,4S)-5-(azepan-1-ylimino)pentane-1,2,3,4-tetrol

Conditions	Yield
In methanol for 3h; Reflux;	85%

1-azepanylamine (5906-35-4) + cyclohexanecarbaldehyde (2043-61-0) → Azepan-1-yl-[1-cyclohexyl-meth-(E)-ylidene]-amine (125142-76-9)

Conditions	Yield
In ethanol for 0.5h; heating on a steam bath;	84%

1-azepanylamine (5906-35-4) + 1,4-diisocyanatobenzene (104-49-4) → 1,1′-(1,4-phenylene)bis(3-(azepan-1-yl)urea)

Conditions	Yield
With N,N'-dimethylpiperazine In tetrahydrofuran at 0 - 50℃; for 4.5h;	84%

pyridine-2-carbaldehyde (1121-60-4) + 1-azepanylamine (5906-35-4) → N-(2-pyridinylmethylene)hexahydro-1H-azepin-1-amine

Conditions	Yield
In methanol at 20℃; for 24h;	83%

1-(4-chlorophenyl)-2-(2,4-dichlorophenyl)-5-methyl-1H-imidazole-4-carboxylic acid (796875-26-8) + 1-azepanylamine (5906-35-4) → 1-(4-chloro-phenyl)-2-(2,4-dichloro-phenyl)-5-methyl-1H-imidazole-4-carboxylic acid azepan-1-ylamide

Conditions	Yield
With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In acetonitrile at 20℃; for 16h;	82%

1-azepanylamine (5906-35-4) + 2-fluoro-5-nitrophenylacetic acid chloride (195609-20-2) → N-(Azepan-1-yl)(2-fluoro-5-nitrophenyl)acetamide (195609-28-0)

Conditions	Yield
With sodium hydrogencarbonate In chloroform for 2h; Ambient temperature;	81%

2-methylthio-2-imidazoline hydroiodide (5464-11-9) + 1-azepanylamine (5906-35-4) → 2-[(1-perhydroazepinyl)]iminoimidazolidine hydriodide

Conditions	Yield
In ethanol for 8h; Condensation; Heating;	81%

Glyoxal (131543-46-9) + 1-azepanylamine (5906-35-4) → N,N'-(1,2-ethanediylidene)bishexahydro-1H-azepin-1-amine

Conditions	Yield
In methanol; water at 20℃; for 1h;	80%

4H-thiopyran-4-one (1003-41-4) + 1-azepanylamine (5906-35-4) → 1-(hexahydro-1H-azepin-1-yl)-4-thiopyridone

Conditions	Yield
In ethanol	79%

piperonal (120-57-0) + 1-azepanylamine (5906-35-4) → N-(1,3-benzodioxol-5-ylmethylene)azepan-1-amine (16987-38-5)

Conditions	Yield
In ethanol for 7.5h; Heating;	79%

Upstream product

• 1310-73-2 sodium hydroxide 
• 99560-25-5 (R)-3-aminoazepan-2-one hydrochloride 
• 629-03-8 1 ,6-dibromohexane 
• 7803-57-8 hydrazine hydrate 
• 21223-22-3 (CH₂)6NNH₂*BH₃ 
• 7732-18-5 water 
• 111-49-9 hexamethylene imine 

Downstream Products

• 21862-36-2 2,2,4-triphenyl-3-oxa-1-aza-6-azonia-2-borata-spiro[5.6]dodecane 
• 21862-35-1 4-methyl-2,2-diphenyl-3-oxa-1-aza-6-azonia-2-borata-spiro[5.6]dodecane 
• 77410-30-1 (S)-2-{4-[(2,4-Diamino-pteridin-6-ylmethyl)-methyl-amino]-benzoylamino}-pentanedioic acid bis-azepan-1-ylamide 
• 851855-10-2 3-(1-azepanylamino)-2,5,5-trimethyl-2-cyclohexen-1-one 
• 851854-89-2 3-(1-azepanylamino)-5,5-dimethyl-2-cyclohexen-1-one 
• 869802-58-4 A-841720 
• 502767-66-0 N-(3-chloro-4-mnethoxy-phenyl)-N,N'-bis-perhydro-azepin-1-yl-1,3,5-triazine-2,4,6-triamine 
• 1103532-91-7 N-azepan-1-yl-5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-1H-pyrazole-4-carboxamide 
• 1058164-45-6 N-(azepan-1-yl)-1-(2,4-dichlorophenyl)-4-methyl-5-(5-(4-methylpent-1-ynyl)thiophen-2-yl)-1H-pyrazole-3-carboxamide 
• 1020106-45-9 N-(azepan-1-yl)-1-(2,4-dichlorophenyl)-4-ethyl-5-(5-(pent-1-ynyl)thiophen-2-yl)-1H-pyrazole-3-carboxamide 
• 1058164-53-6 N-(azepan-1-yl)-5-(5-(but-1-ynyl)thiophen-2-yl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carboxamide 
• 1058164-55-8 N-(azepan-1-yl)-1-(2,4-dichlorophenyl)-5-(5-(hex-1-ynyl)thiophen-2-yl)-4-methyl-1H-pyrazole-3-carboxamide 
• 951780-40-8 C₁₅H₁₉ClF₃N₃O₂S 

Relevant articles and documents

N-Amino-1,8-Naphthalimide is a Regenerated Protecting Group for Selective Synthesis of Mono-N-Substituted Hydrazines and Hydrazides

A new route to synthesis of various mono-N-substituted hydrazines and hydrazides by involving in a new C?N bond formation by using N-amino-1,8-naphthalimide as a regenerated precursor was invented. Aniline and phenylhydrazines are reproduced upon reacting these individually with 1,8-naphthalic anhydride followed by hydrazinolysis. The practicality and simplicity of this C?N dihalo alkanes; developed a synthon for bond formation protocol was exemplified to various hydrazines and hydrazides. N-amino-1,8-naphthalimide is suitable synthon for transformation for selective formation of mono-substituted hydrazine and hydrazide derivatives. Those are selective mono-amidation of hydrazine with acid halides; mono-N-substituted hydrazones from aldehydes; synthesis of N-aminoazacycloalkanes from acetohydrazide scaffold and inserted to hydroxy derivatives; distinct synthesis of N,N-dibenzylhydrazines and N-benzylhydrazines from benzyl halides; synthesis of N-amino-amino acids from α-halo esters. Ecofriendly reagent N-amino-1,8-naphthalimide was regenerated with good yields by the hydrazinolysis in all procedures.

3-AMINOPIPERIDINE DERIVATIVES AS INTEGRIN γ(a)vγ(b)3 ANTAGONISTS

An object of the present invention is to provide novel derivatives having integrin αvβ3 antagonistic activity wherein a basic atomic group has been attached to the 3-position of a piperidine ring either directly or through various atomic groups. The derivatives according to the present invention are compounds represented by formula (I) or pharmaceutically acceptable salts or solvates thereof, which are useful for the treatment or prevention of cardiovascular diseases, angiogenesis-related diseases, cerebrovascular diseases, cancers and metastasis thereof, immunological diseases, osteopathy and other diseases: wherein A represents an optionally substituted heterocyclic group containing at least one nitrogen atom, a bicylic group or the like; D represents a bond, >NR4, >CR5R6, O, S, or -NR4-CR5R6-; Z represents CH or N; R7 and R8 represent hydroxyl, alkyl or the like; Q represents >C=O or the like; R9 represents hydrogen, alkyl or the like; J represents a bond or alkylene; R10 represents optionally substituted hydroxyl, amino or the like; R11 represents hydrogen, alkyl or the like; m is 0 to 5; n is 0 to 4; p is 3 or 4; and q is 0 to 3.