4897-50-1

Basic information

• Product Name: 4-Piperidinopiperidine
• Synonyms: 1-(4-PIPERIDINO)PIPERIDINE, 99%;1-Piperidin-4-ylpiperidine;4-Piperidinopiperidine ,98%;1-(4-Piperidinyl)piperidine;1-(Piperidine-4-yl)piperidine;4-Piperidinopiperidine,95%,tech.;4-piperidine-piperdine;4-Piperidinopiperid
• CAS NO: 4897-50-1
• Molecular Formula: C₁₀H₂₀N₂
• Molecular Weight: 168.28
• EINECS: 225-522-8
• Product Categories: Nitrogen cyclic compounds;PHARMACEUTICAL INTERMEDIATES;Heterocycles;Piperidine;Heterocyclic Compounds;Piperidine Series;Piperidines;Bioactive Small Molecules;Building Blocks;C10;Cell Biology;Chemical Synthesis;Heterocyclic Building Blocks;P
• Mol File: 4897-50-1.mol
• Article Data: 6

Chemical Properties

• Melting Point: 64-66 °C(lit.)
• Boiling Point: 287.25°C (rough estimate)
• Flash Point: 99.9 °C
• Appearance: Light yellow to yellow-brown/Crystalline Solid
• Density: 0.9725 (rough estimate)
• Vapor Pressure: 0.0205mmHg at 25°C
• Refractive Index: 1.6011 (estimate)
• Storage Temp.: ?20°C
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 10.31±0.10(Predicted)
• CAS DataBase Reference: 4-Piperidinopiperidine(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Piperidinopiperidine(4897-50-1)
• EPA Substance Registry System: 4-Piperidinopiperidine(4897-50-1)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-24/25
• WGK Germany: 3
• HazardClass: 8
• Hazardous Substances Data: 4897-50-1(Hazardous Substances Data)

Usage

Chemical Properties

light yellow to yellow-brown crystalline solid

Uses

Different sources of media describe the Uses of 4897-50-1 differently. You can refer to the following data:
1. Reactant for synthesis of: Arylthiadiazole H3 antagonists1 Water-soluble N-mustards as anticancer agents2 Antitubercular drugs3 Vasopressin1b receptor antagonists4 MDR modulators5 Selective Norepinephrine transporter inhibitors6
2. Reactant for synthesis of: Arylthiadiazole H3 antagonists Water-soluble N-mustards as anticancer agents Antitubercular drugs Vasopressin1b receptor antagonists MDR modulators Selective Norepinephrine transporter inhibitors

InChI:InChI=1/C10H20N2/c1-2-8-12(9-3-1)10-4-6-11-7-5-10/h10-11H,1-9H2/p+2

Synthetic route

piperidine (110-89-4) + N-tert-butyloxycarbonylpiperidin-4-one (79099-07-3) → 4-piperidinopiperidin (4897-50-1)

Conditions	Yield
With sodium tris(acetoxy)borohydride; acetic acid In dichloromethane at 0 - 20℃; for 16h;	80%

4-methoxy-7-morpholin-4-yl-benzothiazol-2-yl-amine (383865-57-4) → 4-piperidinopiperidin (4897-50-1) + [1,4']Bipiperidinyl-1'-carboxylic acid (4-methoxy-7-morpholin-4-yl-benzothiazol-2-yl)-amide

Conditions	Yield
	A n/a B 35%

irinotecan (97682-44-5, 130144-33-1) → 4-piperidinopiperidin (4897-50-1) + 7-ethyl-10-hydroxycamptothecin (86639-52-3, 110714-48-2, 130144-34-2)

Conditions	Yield
With carboxylesterase at 37℃; for 0.0833333h; pH=7.4;

[1,4']bipiperidinyl-1'-carboxylic acid (4-bromo-phenyl)amide (944411-93-2) → 4-piperidinopiperidin (4897-50-1) + [1,4']bipiperidinyl-1'-carboxylic acid (3'-acetylamino-biphenyl-4-yl)amide + C14H14N2O (1608129-84-5) + 4-bromo-aniline (106-40-1)

Conditions	Yield
Suzuki-Miyaura Coupling;

N-tert-butyloxycarbonylpiperidin-4-one (79099-07-3) → 4-piperidinopiperidin (4897-50-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: acetic acid; sodium tris(acetoxy)borohydride / dichloromethane / 16 h / 0 - 20 °C 2: hydrogenchloride / methanol / 12 h / 40 °C View Scheme

tert-butyl 1,4’-bipiperidine-1’-carboxylate (125541-12-0) → 4-piperidinopiperidin (4897-50-1)

Conditions	Yield
With hydrogenchloride In methanol at 40℃; for 12h;	2.04 g

4-piperidinopiperidin (4897-50-1) + 5-fluoro-2-nitroaniline (2369-11-1) → 2-nitro-5-(4-(piperidin-1-yl)piperidin-1-yl)benzenamine (900506-32-3)

Conditions	Yield
With triethylamine In 1-methyl-pyrrolidin-2-one at 100℃; for 2.5h;	100%
With N-ethyl-N,N-diisopropylamine In 1-methyl-pyrrolidin-2-one at 120℃; for 4h;	75%

4-piperidinopiperidin (4897-50-1) + [Bis(methylthio)methylene]malononitrile (5147-80-8) → [(methylthio)(4-piperidinopiperidino)methylene]malononitrile (904677-87-8)

Conditions	Yield
In tetrahydrofuran at 0 - 20℃; for 0.25h;	100%

4-piperidinopiperidin (4897-50-1) + 2-tert-butyloxycarbonylamino-3-(3,4-dichlorophenyl)propionic acid (185321-62-4) → C24H35Cl2N3O3

Conditions	Yield
With benzotriazol-1-ol; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide	100%

4-piperidinopiperidin (4897-50-1) + N6-Boc-N2-Cbz-lysine (215595-66-7) → C29H46N4O5

Conditions	Yield
	100%

4-piperidinopiperidin (4897-50-1) + (R)-3-((2R,3S)-2-((E)-3-fluorostyryl)-4-oxo-3-((S)-2-oxo-4-phenyloxazolidin-3-yl)azetidin-1-yl)-4-oxo-4-(((R)-1-phenylethyl)amino)butanoic acid (1361214-48-3) → (R)-4-([1,4'-bipiperidin]-1'-yl)-2-((2R,3S)-2-((E)-3-fluorostyryl)-4-oxo-3-((S)-2-oxo-4-phenyloxazolidin-3-yl)azetidin-1-yl)-4-oxo-N-((R)-1-phenylethyl)butanamide (1361214-50-7)

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 18h;	100%

4-piperidinopiperidin (4897-50-1) + bis(trichloromethyl) carbonate (32315-10-9) → 4-piperidinopiperidine-1-carbonyl chloride (103816-19-9)

Conditions	Yield
With triethylamine In dichloromethane at -10 - 20℃; for 4h;	99%
Stage #1: 4-piperidinopiperidin; bis(trichloromethyl) carbonate In dichloromethane; acetonitrile at 20 - 70℃; Stage #2: With potassium carbonate In dichloromethane at 20℃;	98.5%
Stage #1: 4-piperidinopiperidin; bis(trichloromethyl) carbonate In hexane; dichloromethane; acetonitrile at 20 - 25℃; Stage #2: With potassium carbonate In dichloromethane at 20℃;	98.5%

4-piperidinopiperidin (4897-50-1) + 4-fluoro-2-methoxy-1-nitrobenzene (448-19-1) → 1'-[3-(methyloxy)-4-nitrophenyl]-1,4'-bipiperidine (761440-29-3)

Conditions	Yield
With potassium carbonate In dimethyl sulfoxide at 20℃; for 72h;	99%

4-piperidinopiperidin (4897-50-1) + 2-(methylthio)oxazolo[4,5-b]pyridine (169205-95-2) → C16H22N4O (1231933-81-5)

Conditions	Yield
In N,N-dimethyl-formamide at 100℃;	99%
In N,N-dimethyl-formamide at 100℃;	90%

4-piperidinopiperidin (4897-50-1) + 5,5-difluoro-10-(p-tolyl)-5H-dipyrrolo[1,2-c:2',1'-f][1,3,2]diazaborinin-4-ium-5-uide (955084-10-3) → C26H31BF2N4

Conditions	Yield
With silver(I) acetate In dimethyl sulfoxide at 80℃; for 12h; Schlenk technique; Inert atmosphere; regioselective reaction;	99%

4-piperidinopiperidin (4897-50-1) + carbonic acid dimethyl ester (616-38-6) → 4-piperidylpiperidine methyl carbonate

Conditions	Yield
In N,N-dimethyl-formamide at 60 - 65℃; for 3h;	98.5%

4-piperidinopiperidin (4897-50-1) + trifluoroacetic acid (76-05-1) + N-Boc pyroglutamic acid-Wang resin → (S)-2-Amino-5-[1,4']bipiperidinyl-1'-yl-5-oxo-pentanoic acid; compound with trifluoro-acetic acid

Conditions	Yield
Stage #1: 4-piperidinopiperidin; N-Boc pyroglutamic acid-Wang resin In tetrahydrofuran Addition; Stage #2: trifluoroacetic acid In water for 2.5h; Hydrolysis;	98%

rac-(3-(3-bromophenyl)-2-tert-butoxycarbonylamino)propionic acid (82278-95-3) + 4-piperidinopiperidin (4897-50-1) → C24H36BrN3O3

Conditions	Yield
With benzotriazol-1-ol; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide	98%

4-piperidinopiperidin (4897-50-1) + 2-{4-amino-3-iodo-1H-pyrazolo[3,4-d]pyrimidin-1-yl}acetaldehyde → 3-iodo-1-[2-[4-(1-piperidyl)-1-piperidyl]ethyl]pyrazolo[3,4-d]pyrimidin-4-amine

Conditions	Yield
Stage #1: 4-piperidinopiperidin; 2-{4-amino-3-iodo-1H-pyrazolo[3,4-d]pyrimidin-1-yl}acetaldehyde With acetic acid In dichloromethane for 0.166667h; Stage #2: With sodium tris(acetoxy)borohydride In dichloromethane for 17h;	97.5%
Stage #1: 4-piperidinopiperidin; 2-{4-amino-3-iodo-1H-pyrazolo[3,4-d]pyrimidin-1-yl}acetaldehyde With acetic acid In dichloromethane for 0.166667h; Stage #2: With sodium tris(acetoxy)borohydride In dichloromethane for 17h;	191.6 mg

4-piperidinopiperidin (4897-50-1) → 2-[1,4']bipiperidinyl-1'-yl-1-(3-methoxy-phenyl)-ethanol (1269606-87-2)

Conditions	Yield
	97%

4-piperidinopiperidin (4897-50-1) + C26H20ClN3O → 4-(((1,4'-bipiperidin)-1'-yl)methyl)-N-(1-(p-methylphenyl)-9H-pyrido[3,4-b]indol-3-yl)benzamide

Conditions	Yield
With potassium carbonate; potassium iodide In acetonitrile for 10h;	97%

4-piperidinopiperidin (4897-50-1) + sulindac sulfide (49627-27-2) → (Z)-1-([1,4'-bipiperidin]-1'-yl)-2-(5-fluoro-2-methyl-1-(4-(methylthio)benzylidene)-1H-inden-3-yl)ethanone

Conditions	Yield
With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; triethylamine In acetonitrile at 20℃; Inert atmosphere;	97%

4-piperidinopiperidin (4897-50-1) + p-(chloromethyl)benzoyl chloride (876-08-4) → 1-(4-chloromethylbenzoyl)-4-piperidinopiperidine hydrochloride

Conditions	Yield
In acetonitrile at 20℃; for 2h;	96%

4-piperidinopiperidin (4897-50-1) + (R)-2-(4-(8-Fluoro-2-oxo-1,2-dihydroquinolin-3-yl)piperidine-1-carbonyloxy)-3-(7-methyl-2-((2-(trimethylsilyl)ethoxy)methyl)-2H-indazol-5-yl)propanoic acid (865626-93-3) → (R)-3-(7-Methyl-2-((2-(trimethylsilyl)ethoxy)methyl)-2H-indazol-5-yl)-1-oxo-1-(4-(piperidin-1-yl)piperidin-1-yl)propan-2-yl 4-(8-fluoro-2-oxo-1,2-dihydroquinolin-3-yl)piperidine-1-carboxylate (865626-94-4)

Conditions

Yield

Stage #1: (R)-2-(4-(8-Fluoro-2-oxo-1,2-dihydroquinolin-3-yl)piperidine-1-carbonyloxy)-3-(7-methyl-2-((2-(trimethylsilyl)ethoxy)methyl)-2H-indazol-5-yl)propanoic acid With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine In DMF (N,N-dimethyl-formamide) at 20℃; for 0.0833333h; Stage #2: 4-piperidinopiperidin In DMF (N,N-dimethyl-formamide) at 20℃; for 2h;

96%

4-piperidinopiperidin (4897-50-1) + 3-chloro-N-(4-nitrophenyl)propanamide (19313-88-3) → 3-([1,4'-bipiperidin]-1'-yl)-N-(4-nitrophenyl)propanamide (1586764-66-0)

Conditions	Yield
In tetrahydrofuran at 50℃;	96%

4-piperidinopiperidin (4897-50-1) + 4-chloromethyl-N-(9H-pyrido[3,4-b]indol-3-yl)benzamide → 4-(((1,4'-bipiperidin)-1'-yl)methyl)-N-(9H-pyrido[3,4-b]indol-3-yl)benzamide

Conditions	Yield
With potassium carbonate; potassium iodide In acetonitrile for 10h;	96%

4-piperidinopiperidin (4897-50-1) + 1-bromomethyl-4-nitro-benzene (100-11-8) → 1'-(4-nitrobenzyl)-1,4'-bipiperidine

Conditions	Yield
In acetonitrile at 20℃; for 2h;	96%
With potassium carbonate; potassium iodide In acetonitrile for 5h;	92%

4-piperidinopiperidin (4897-50-1) + 2-{2[(tert-butoxycarbonyl)amino]-1,3-thiazol-4-yl}acetic acid (89336-46-9) → tert-butyl {4-[2-(1,4’-bipiperidin-1‘-yl)-2-oxoethyl]-1,3-thiazol-2-yl}carbamate

Conditions	Yield
With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl acetamide at 20℃;	96%

4-piperidinopiperidin (4897-50-1) + C18H17Cl3N6 → 5-(4-(piperidin-1-yl)piperidin-1-yl)methyl-7-(4-(bis(2-chloroethyl)amino)phenylamino)-3-cyanopyrazolo[1,5-a]pyrimidine

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 40℃;	95.3%

4-piperidinopiperidin (4897-50-1) + 6-((3-fluorobenzyl)amino)imidazo[1,2-b]pyridazine-3-carboxylic acid → [1,4'-bipiperidin]-1'-yl(6-((3-fluorobenzyl)amino)imidazo[1,2-b]pyridazin-3-yl)methanone

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 60℃; for 1h;	95.1%

4-piperidinopiperidin (4897-50-1) + 7-chloro-3,6-dicyano-2-ethoxy-4-phenyl-1,8-naphthyridine (583051-10-9) → 3,6-dicyano-2-ethoxy-4-phenyl-7-(4-piperidylpiperidino)-1,8-naphthyridine

Conditions	Yield
With triethylamine In tetrahydrofuran for 16h; Heating;	95%

4-piperidinopiperidin (4897-50-1) + C14H18Br2N2O4 → C24H36Br2N4O3

Conditions	Yield
With benzotriazol-1-ol; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide	95%

5-(3-bromophenyl)-3H-1,3,4-oxadiazol-2-one (873090-18-7) + 4-piperidinopiperidin (4897-50-1) → 1'-[5-(3-bromophenyl)-1,3,4-oxadiazol-2-yl]-1,4'-bipiperidinyl (1024613-87-3)

Conditions	Yield
With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 18h;	95%

Upstream product

• 19099-93-5 benzyl 4-oxo-1-piperidinecarboxylate 
• 110-89-4 piperidine 
• 125541-12-0 tert-butyl 1,4’-bipiperidine-1’-carboxylate 
• 79099-07-3 N-tert-butyloxycarbonylpiperidin-4-one 
• 944411-93-2 [1,4']bipiperidinyl-1'-carboxylic acid (4-bromo-phenyl)amide 
• 97682-44-5 irinotecan 
• 383865-57-4 4-methoxy-7-morpholin-4-yl-benzothiazol-2-yl-amine 

Downstream Products

• 188721-66-6 1-methyl-2-(4-chlorophenoxymethyl)-3-[2-[4-(piperidin-1-yl)piperidin-1-yl]-1,2-ethanedionyl]-1H-indole 
• 863030-25-5 7-(3-[1,4'-bipiperidin]-1'-ylpropoxy)-4-[(2,4-dichloro-5-methoxyphenyl)amino]-6-methoxy-3-quinolinecarbonitrile 
• 863030-22-2 7-(2-[1,4']bipiperidinyl-1'-yl-ethoxy)-6-methoxy-4-(4-phenoxy-phenylamino)-quinoline-3-carbonitrile 
• 334942-08-4 benzyl [1,4']bipiperidinyl-1'-acetate 

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Supramolecular helical self-assemblies and large stokes shift in 1-(2-cyanophenyl)piperazine and 4-Piperidinopiperidine (cas 4897-50-1) bis-substituted tetracyanoquinodimethane fluorophores07/12/2019

Heterocyclic building blocks such as 1-(2-cyanophenyl)piperazine (1,2-CPP) and 4-piperidinopiperidine (4-PP) are very well known in oncological medicines like platins and camptothecins. Utilization of 1,2-CPP and 4-PP in the reaction with tetracyanoquinodimethane (TCNQ) produced two latest compo...detailed

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