140-80-7

Basic information

• Product Name: 2-Amino-5-diethylaminopentane
• Synonyms: 4-AMINO-1-DIETHYLAMINOPENTANE;5-DIETHYLAMINO-2-AMINOPENTANE;1,4-Pentanediamine, N1,N1-diethyl-;4-aminopentyldiethylamine;PAROXETINE HYDROCHLORIDE ,(-)TRANS-3-[(1,3-BENZODIOXOL-5-YLOXY) METHYL]-4-(4-FLUOROPHENYL) PAROXETINE HYDROCHLORIDE;N1,N1-Diethyl-1,4-pentanediamine;δ-Diethylamino-α-methylbutylamine;2-AMINO-5-DIETHYLAMINOPENTANE(NOVOLDIAMINE)
• CAS NO: 140-80-7
• Molecular Formula: C₉H₂₂N₂
• Molecular Weight: 158.28
• EINECS: 205-435-1
• Product Categories: API
• Mol File: 140-80-7.mol
• Article Data: 7

Chemical Properties

• Melting Point: 37.5°C (estimate)
• Boiling Point: 101 °C / 37mmHg
• Flash Point: 155 °F
• Appearance: Colorless clear liquid
• Density: 0.817 g/mL at 25 °C(lit.)
• Vapor Pressure: 2.39E-08mmHg at 25°C
• Refractive Index: n20/D 1.4429(lit.)
• PKA: 10.81±0.35(Predicted)
• Merck: 14,6723
• CAS DataBase Reference: 2-Amino-5-diethylaminopentane(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Amino-5-diethylaminopentane(140-80-7)
• EPA Substance Registry System: 2-Amino-5-diethylaminopentane(140-80-7)

Safety Data

• Hazard Codes: C
• Statements: 34
• Safety Statements: 26-36/37/39-45
• RIDADR: UN 2946 6.1/PG 3
• WGK Germany: 1
• RTECS: XE1900000
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 140-80-7(Hazardous Substances Data)

Usage

Chemical Properties

Colorless liquid.Soluble in water and alcohol.

Uses

manufacture of quinacrine and other antimalarials having the same basic side chain.

General Description

A colorless liquid. Toxic by ingestion, inhalation and skin absorption. Irritating to skin and eyes. Used to make other chemicals.

Reactivity Profile

2-Amino-5-diethylaminopentane neutralizes acids in exothermic reactions to form salts plus water. May be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen may be generated in combination with strong reducing agents, such as hydrides.

Health Hazard

TOXIC; inhalation, ingestion or skin contact with material may cause severe injury or death. Contact with molten substance may cause severe burns to skin and eyes. Avoid any skin contact. Effects of contact or inhalation may be delayed. Fire may produce irritating, corrosive and/or toxic gases. Runoff from fire control or dilution water may be corrosive and/or toxic and cause pollution.

Fire Hazard

Combustible material: may burn but does not ignite readily. When heated, vapors may form explosive mixtures with air: indoors, outdoors and sewers explosion hazards. Contact with metals may evolve flammable hydrogen gas. Containers may explode when heated. Runoff may pollute waterways. Substance may be transported in a molten form.

InChI:InChI=1/2C19H20FNO3.2ClH.H2O/c2*20-15-3-1-13(2-4-15)17-7-8-21-10-14(17)11-22-16-5-6-18-19(9-16)24-12-23-18;;;/h2*1-6,9,14,17,21H,7-8,10-12H2;2*1H;1H2/t2*14-,17-;;;/m00.../s1

Synthetic route

(R)-(-)-4-amino-1-(diethylamino)pentane (67459-50-1) → 5-diethylamino-2-pentylamine (140-80-7)

Conditions	Yield
With nickel In toluene at 70℃; for 12h;	97.2%

5-diethylaminopentan-2-ol (5412-69-1) → 5-diethylamino-2-pentylamine (140-80-7)

Conditions	Yield
With ammonia; nickel at 200℃; unter Druck;
With ammonia; nickel at 200℃; unter Druck;

diethyl-(4-chloro-pentyl)-amine (39749-10-5) → N1,N1-diethyl-1-methyl-butanediyldiamine (344325-82-2) + 5-diethylamino-2-pentylamine (140-80-7)

Conditions	Yield
With potassium phthalide; xylene at 150 - 160℃; anschl. Erwaermen mit HCl;

5-diethylamino-2-pentanone (105-14-6) → 5-diethylamino-2-pentylamine (140-80-7)

Conditions	Yield
With methanol; ammonia; nickel at 95 - 96℃; under 36775.4 Torr; Hydrogenation;
With ethanol; ammonia at 40℃;
Multi-step reaction with 2 steps 1: ethanol; Raney nickel; NH3 / Hydrogenation 2: methanol; nickel catalyst; hydrogen; NH3 / 14710.2 Torr View Scheme
With methanol; ammonia; nickel at 70 - 80℃; Hydrogenation.unter Druck;

5-diethylamino-2-pentanone (105-14-6) → bis-(4-diethylamino-1-methyl-butyl)-amine (101881-56-5) + 5-diethylamino-2-pentylamine (140-80-7)

Conditions	Yield
With ethanol; ammonia at 20℃;
With ethanol; ammonia; nickel Hydrogenation;

5-diethylamino-pentan-2-one oxime (5426-96-0) → 5-diethylamino-2-pentylamine (140-80-7)

Conditions	Yield
With ethanol; sodium

bis-(4-diethylamino-1-methyl-butyl)-amine (101881-56-5) → 5-diethylamino-2-pentylamine (140-80-7)

Conditions	Yield
With methanol; ammonia; hydrogen; nickel under 14710.2 Torr;

hydrogenchloride (7647-01-0) + pamaquine (491-92-9) + water (7732-18-5) + NaNO2 → 6-methoxy-quinolin-8-ol (477601-28-8) + 5-diethylamino-2-pentylamine (140-80-7)

Conditions	Yield
anschl. mit methanol. KOH;

methanol (67-56-1) + bis-(4-diethylamino-1-methyl-butyl)-amine (101881-56-5) + ammonia (7664-41-7) + hydrogen + nickel catalyst → 5-diethylamino-2-pentylamine (140-80-7)

Conditions	Yield
under 14710.2 Torr;

5-diethylamino-2-pentanone (105-14-6) + ammonia (7664-41-7) + nickel → 5-diethylamino-2-pentylamine (140-80-7)

Conditions	Yield
Hydrogenation;

5-diethylamino-2-pentanone (105-14-6) + methanol.NH3 + nickel → 5-diethylamino-2-pentylamine (140-80-7)

Conditions	Yield
Hydrogenation;

(4-diethylamino-1-methyl-butyl)-dithiocarbamic acid (18997-67-6) → 5-diethylamino-2-pentylamine (140-80-7) + CS2

Conditions	Yield
durch Saeuren;
durch Saeuren;

2-(diethylamino)acetaldehyde (32314-21-9) → 5-diethylamino-2-pentylamine (140-80-7)

Conditions	Yield
Multi-step reaction with 3 steps 1: alkaline solution 2: Raney nickel / Hydrogenation 3: ethanol; NH3 / 40 °C View Scheme

5-diethylamino-pent-3-en-2-one (136571-69-2) → 5-diethylamino-2-pentylamine (140-80-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: Raney nickel / Hydrogenation 2: ethanol; NH3 / 40 °C View Scheme

C9H22N2*C8H8O3 → 5-diethylamino-2-pentylamine (140-80-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium hydroxide / water / pH 11 - 12 2: nickel / toluene / 12 h / 70 °C View Scheme

11-chloro-5-methyl-5H-indolo[2,3-b]quinoline (1150313-28-2) + 5-diethylamino-2-pentylamine (140-80-7) → N1,N1-diethyl-N4-(5-methyl-5H-indolo[2,3-b]quinolin-11-yl)pentane-1,4-diamine (1150313-32-8)

Conditions	Yield
In N,N-dimethyl-formamide at 135 - 155℃;	99%
Heating;	98%
at 80 - 120℃;	98%
at 135 - 155℃; Neat (no solvent);	77%

3-(1-hydroxyhexylidene)-5-(2-(methylthio)ethyl)-1-(3,5,5-trimethylhexanoyl)pyrrolidine-2,4-dione + 5-diethylamino-2-pentylamine (140-80-7) → C31H57N3O3S

Conditions	Yield
In toluene Reflux;	99%

1-benzoyl-3-(1-hydroxy-4-phenoxybutylidene)-5-isobutylpyrrolidine-2,4-dione + 5-diethylamino-2-pentylamine (140-80-7) → C34H47N3O4

Conditions	Yield
In toluene Reflux;	99%

2-chloro-4-hydroxy-quinazoline (607-69-2) + 5-diethylamino-2-pentylamine (140-80-7) → 2-<<4-(diethylamino)-1-methylbutyl>amino>-4-quinazolinol (76005-48-6)

Conditions	Yield
In ethanol for 14h; Heating;	97%

perylene-3,4,9,10-tetracarboxylic acid 3,4:9,10-dianhydride (128-69-8) + 5-diethylamino-2-pentylamine (140-80-7) → N,N'-bis(4-diethylamino-1-methylbutyl)perylene-3,4:9,10-tetracarboxylic acid bisimide (106409-01-2)

Conditions	Yield
With 1H-imidazole at 160℃; for 16h;	97%

5-diethylamino-2-pentylamine (140-80-7) + 8-amino-4,6-dichloroquinoline (181189-00-4) → 8-amino-6-chloro-4-(4-diethylamino-1-methylbutyl)aminoquinoline (181189-01-5)

Conditions	Yield
at 180℃; for 16h;	96%

1-[7-chloro-4-(dimethylamino)quinolin-3-yl]-2,2,2-trifluoroethan-1-one (501947-42-8) + 5-diethylamino-2-pentylamine (140-80-7) → 1-[7-chloro-4-(5-diethylaminopentan-2-ylamino)quinolin-3-yl]-2,2,2-trifluoroethan-1-one

Conditions	Yield
In acetonitrile for 8h; Reflux;	95%

2-azidobenzaldehyde (16714-25-3) + 5-diethylamino-2-pentylamine (140-80-7) → C16H25N3

Conditions	Yield
at 100℃; under 10343.2 Torr; Microwave irradiation;	95%

(S)-Mandelic acid (17199-29-0) + 5-diethylamino-2-pentylamine (140-80-7) → C9H22N2*C8H8O3

Conditions	Yield
In isopropyl alcohol at 20℃;	94.9%

(R)-Mandelic Acid (611-71-2) + 5-diethylamino-2-pentylamine (140-80-7) → C9H22N2*C8H8O3

Conditions	Yield
In isopropyl alcohol at 20℃; for 3h;	94.9%
In isopropyl alcohol at 20℃; for 3h;	94.9%

4,7-dichloroquinoline (86-98-6) + 5-diethylamino-2-pentylamine (140-80-7) → Chloroquine (54-05-7)

Conditions	Yield
With diethylamine; phenol at 90 - 100℃; under 1140.08 Torr; Temperature; Reagent/catalyst; Pressure;	90.72%
With indium(III) chloride In acetonitrile at 120℃; for 1h; Microwave irradiation; regioselective reaction;	73%
1.) 100 deg C, 2 h, 2.) 150-160 deg C, 5 h;
at 135 - 140℃; for 24h;
With N-ethyl-N,N-diisopropylamine; sodium sulfite In isopropyl alcohol at 133 - 138℃; for 10h;	137.5 g

5-diethylamino-2-pentylamine (140-80-7) + 4-bromoquinoline (3964-04-3) → 4-(4-diethylamino-1-methylbutylamino)-quinoline (1915-92-0)

Conditions	Yield
With potassium phosphate; bis[2-(diphenylphosphino)phenyl] ether; palladium diacetate In 1,4-dioxane at 85℃; for 18h;	88%

5-diethylamino-2-pentylamine (140-80-7) + formic acid ethyl ester (109-94-4) → N,N-diethyl-4-isocyanopentan-1-amine

Conditions	Yield
Stage #1: 5-diethylamino-2-pentylamine; formic acid ethyl ester for 16h; Reflux; Stage #2: With bis(trichloromethyl) carbonate; N-ethyl-N,N-diisopropylamine In dichloromethane at -40 - 0℃; for 2h;	88%

3-hydroxy-2-methylene-3-(2-nitrophenyl)propanoic acid methyl ester (159763-36-7) + 5-diethylamino-2-pentylamine (140-80-7) → methyl 2-[(4-diethylamino-1-methylbutyl)amino-methy]-3-hydroxy-3-(2-nitrophenyl)propanoate

Conditions	Yield
With triethylamine In tetrahydrofuran for 48h;	87%

5-diethylamino-2-pentylamine (140-80-7) + 4-chloro-2-methylquinoline-6-carboxylic acid (181189-02-6) → 4-(4-diethylamino-1-methylbutyl)amino-2-methylquinoline-6-carboxylic acid (181189-03-7)

Conditions	Yield
at 150℃; for 5.5h;	86%

4,8-dichloroquinoline (21617-12-9) + 5-diethylamino-2-pentylamine (140-80-7) → N4-(8-chloro-4-quinolinyl)-N1,N1-diethyl-1,4-pentanediamine (32668-65-8)

Conditions	Yield
1.) 100 deg C, 2 h, 2.) 140-150 deg C, 7 h;	85%
at 170℃;

1,11-dichloro-5-methyl-5H-indolo[2,3-b]quinoline (1150313-29-3) + 5-diethylamino-2-pentylamine (140-80-7) → N4-(1-chloro-5-methyl-5H-indolo[2,3-b]quinolin-11-yl)-N1,N1-diethyl-pentane-1,4-diamine (1150313-33-9)

Conditions	Yield
at 135 - 155℃; Neat (no solvent);	85%

11-Chlor-5,10-dimethyl-10H-indolo<3,2-b>chinolinium-chlorid + 5-diethylamino-2-pentylamine (140-80-7) → (R,S)-11-(4-Diethylamino-2-pentyl)-amino-5,10-dimethyl-10H-indolo<3,2-b>chinolinium-chlorid-hydrochlorid

Conditions	Yield
In ethanol at 70℃; for 4h;	84%

11-chloro-2-methoxychromeno[2,3-b]indole (1416412-79-7) + 5-diethylamino-2-pentylamine (140-80-7) → C25H31N3O2 (1453096-24-6)

Conditions	Yield
at 80℃;	84%

C25H35NO6 (1603109-75-6) + 5-diethylamino-2-pentylamine (140-80-7) → C34H55N3O5 (1603109-04-1)

Conditions	Yield
In toluene Reflux;	84%

5-(benzyloxy)-4-chloro-6-methoxyquinazoline (120075-53-8) + 5-diethylamino-2-pentylamine (140-80-7) → N4-(5-Benzyloxy-6-methoxy-quinazolin-4-yl)-N1,N1-diethyl-pentane-1,4-diamine (120075-68-5)

Conditions	Yield
With triethylamine In ethanol for 24h; Ambient temperature;	83%

7-chloro-5-methyl-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine (885461-50-7) + 5-diethylamino-2-pentylamine (140-80-7) → C16H25F3N6

Conditions	Yield
In ethanol at 20℃; for 43h;	83%

C23H19N5O3S + 5-diethylamino-2-pentylamine (140-80-7) → (4″RS,2‴RS)-5-[3-(6-Amino-5-cyano-3-methyl-4-isopropyl-2,4-dihydropyrano[2,3-c]pyrazol-4-yl)-5-cyanophenyl]-N-[5-(diethylamino)pent-2-yl]thiophene-2-carboxamide

Conditions	Yield
With 1,1'-carbonyldiimidazole In tetrahydrofuran at 25℃; for 0.5h;	83%

1-(β-carboxyethyl)-1,2,3,4-tetrahydroquinoline (91641-02-0) + 5-diethylamino-2-pentylamine (140-80-7) → N-(5-(diethylamino)pentan-2-yl)-3-(3,4-dihydroquinolin-1(2H)-yl)propanamide

Conditions	Yield
Stage #1: 1-(β-carboxyethyl)-1,2,3,4-tetrahydroquinoline With O-(N-succinimidyl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 0.5h; Stage #2: 5-diethylamino-2-pentylamine In N,N-dimethyl-formamide at 20℃; for 1h;	82.5%

3,11-dichloro-6H-indolo[2,3-b]quinoline (1150313-26-0) + 5-diethylamino-2-pentylamine (140-80-7) → N4-(3-chloro-6H-indolo[2,3-b]quinolin-11-yl)-N1,N1-diethyl-pentane-1,4-diamine (1150313-44-2)

Conditions	Yield
at 20 - 155℃; for 13h;	82%

2-bromo-11-chloro-5-methyl-5H-indolo[2,3-b]quinoline (1356825-65-4) + 5-diethylamino-2-pentylamine (140-80-7) → N4-(2-bromo-5-methyl-5H-indolo[2,3-b]quinolin-11-yl)-N1,N1-diethylpentane-1,4-diamine (1393344-27-8)

Conditions	Yield
In N,N-dimethyl-formamide at 135 - 155℃;	82%
Heating;	64%

2,11-dichlorochromeno[2,3-b]indole (1416412-74-2) + 5-diethylamino-2-pentylamine (140-80-7) → C24H28ClN3O (1453096-22-4)

Conditions	Yield
at 80℃;	82%

C11H9Cl2N (1536007-04-1) + 5-diethylamino-2-pentylamine (140-80-7) → N4-(7-chloro-2-ethylquinolin-4-yl)-N1,N1-diethylpentane-1,4-diamine (1536007-16-5)

Conditions	Yield
With samarium(III) trifluoromethanesulfonate at 140℃; for 48h; Inert atmosphere;	82%

2‑(methanesulfonyl)‑4‑methyl‑6‑(4‑methylphenyl)pyrimidine + 5-diethylamino-2-pentylamine (140-80-7) → N‑[5‑(diethylamino)pentan‑2‑yl]‑4‑methyl‑6‑(4‑methylphenyl)pyrimidin‑2‑amine

Conditions	Yield
In tetrahydrofuran at 120℃; for 13h; Microwave irradiation;	81%

Upstream product

• 105-14-6 5-diethylamino-2-pentanone 
• 7647-01-0 hydrogenchloride 
• 491-92-9 pamaquine 
• 7732-18-5 water 
• 18997-67-6 (4-diethylamino-1-methyl-butyl)-dithiocarbamic acid 
• 67459-50-1 (R)-(-)-4-amino-1-(diethylamino)pentane 
• 136571-69-2 5-diethylamino-pent-3-en-2-one 
• 32314-21-9 2-(diethylamino)acetaldehyde 
• 7664-41-7 ammonia 
• 67-56-1 methanol 
• 101881-56-5 bis-(4-diethylamino-1-methyl-butyl)-amine 
• 5426-96-0 5-diethylamino-pentan-2-one oxime 
• 39749-10-5 diethyl-(4-chloro-pentyl)-amine 
• 5412-69-1 5-diethylaminopentan-2-ol 

Downstream Products

• 802948-70-5 N-(4-diethylamino-1-methyl-butyl)-phthalimide 
• 5443-04-9 N⁴,N⁴-diethyl-N¹-(7-chloro-[2]quinolyl)-1-methyl-butanediyldiamine 
• 5423-84-7 N⁴,N⁴-diethyl-N¹-(4-methoxymethyl-6-methyl-pyrimidin-2-yl)-1-methyl-butanediyldiamine 
• 47352-76-1 N⁴,N⁴-diethyl-1-methyl-N¹-(3,6,7-trimethyl-[4]quinolyl)-butanediyldiamine 
• 47546-41-8 N¹,N¹-diethyl-N⁴-(2-phenylquinolin-4-yl)pentane-1,4-diamine 
• 5428-67-1 N¹-(8-ethoxy-3-methyl-[4]quinolyl)-N⁴,N⁴-diethyl-1-methyl-butanediyldiamine 
• 5423-93-8 N¹,N¹-diethyl-N⁴-1,5-naphthyridin-4-ylpentane-1,4-diamine 
• 83-89-6 quinacrine 
• 94712-89-7 N¹,N¹-diethyl-N⁴-[6-(4-chloro-phenyl)-[1,2,4]triazolo[4,3-b]pyridazin-8-yl]-pentane-1,4-diamine 
• 858419-99-5 3-(4-diethylamino-1-methyl-butyl)-7,8-dimethoxy-2-methyl-3H-quinazolin-4-one 
• 1243-14-7 3,4,5-trimethoxy-benzoic acid-(4-diethylamino-1-methyl-butylamide) 
• 70945-69-6 1,4-Bis-(4-diethylamino-1-methyl-butylamino)-5,8-dihydroxy-anthraquinone 
• 54-05-7 Chloroquine 

Relevant articles and documents

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Application of chiral chloroquine, hydroxychloroquine or salt of the chiral chloroquine and hydroxychloroquine as anti-coronavirus drug target 3CL hydrolase inhibitor for reducing cardiotoxicity

The invention discloses an application of chiral chloroquine, hydroxychloroquine or pharmaceutically acceptable salts of the chiral chloroquine and hydroxychloroquine in preparation of drugs used forpreventing and/or treating coronavirus pneumonia by using a coronavirus key drug target 3CL hydrolase (Mpro) as an action target. The chiral chloroquine and hydroxychloroquine have high bonding strength with the Mpro causing inflammation of the lung and the like; the activity of the Mpro can be significantly inhibited; and the chiral chloroquine and hydroxychloroquine are indicated to have the effect of preventing and treating pneumonia caused by coronaviruses and be able to be used as anti-pneumonia drugs. Through evaluation on the inhibitory activity of an hERG potassium ion channel, the concentration at which the chloroquine, hydroxychloroquine and enantiomers of the chloroquine and hydroxychloroquine are likely to generate cardiotoxicity to the hERG potassium ion channel is provided. The chiral chloroquine and hydroxychloroquine are prepared through chiral high-performance liquid chromatography and chiral synthesis; S-configuration chloroquine, hydroxychloroquine or salts of the chloroquine and hydroxychloroquine can be selected as a drug independently, or form a pharmaceutical composition for treating diseases caused by the coronaviruses; and due to higher activity and low cardiotoxicity of the chloroquine, hydroxychloroquine or salts of the chloroquine and hydroxychloroquine, the administration dosage range is greatly widened.

2-aminopyridine derivatives and combinatorial libraries thereof

The present invention relates to novel 2-aminopyridine derivative compounds of the following formula: wherein R1to R5have the meanings provided herein. The invention further relates to combinatorial libraries containing two or more such compounds, as well as methods of preparing 2-aminopyridine derivative compounds.

2'-(4,6-Disubstituted)-s-triazin-2-yl)amino-6'-dialkylamino flurans

Fluorans useful as color precursors, particularly in the art of carbonless duplicating are normally colorless and are represented by the structural formula STR1 wherein R represents non-tertiary alkyl of one to four carbon atoms; R1 and R2 represent hydrogen or non-tertiary alkyl of one to four carbon atoms; R3 and R4 represent chlorine, NH2 or one of the groups --NR5 -(lower-alkylene)-N(R6)(R7), --NR5 -(lower-alkylene-N(R8)(R9)(R10) An, -NR5 -(lower-alkylene)-OH, -NR5 -(lower-alkylene) STR2 --NR5 -(HSO3 -C6 H4) or --O-(lower-alkylene)-N(R8)(R9) in which R5, R6 and R7 represent hydrogen or non-tertiary alkyl of one to four carbon atoms; R8 and R9 represent non-tertiary alkyl of one to four carbon atoms; R10 represents non-tertiary alkyl of one to four carbon atoms, benzyl or benzyl substituted in the benzene ring by one or two of halo or alkyl of one to three carbon atoms; and An represents an anion.