4-Piperidinopiperidine Chemical Properties

Melting point:

64-66 °C (lit.)

Boiling point:

287.25°C (rough estimate)

Density 

0.9725 (rough estimate)

refractive index 

1.6011 (estimate)

storage temp. 

-20°C

solubility 

Chloroform (Slightly), Methanol (Slightly)

form 

Crystalline Solid

pka

10.31±0.10(Predicted)

color 

Light yellow to yellow-brown

InChI

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

InChIKey

QDVBKXJMLILLLB-UHFFFAOYSA-N

SMILES

N1(C2CCNCC2)CCCCC1

CAS DataBase Reference

4897-50-1(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36-24/25

WGK Germany 

3

HazardClass 

8

HS Code 

29339900

MSDS

• Language:English Provider:4-Piperidinopiperidine
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

4-Piperidinopiperidine Usage And Synthesis

Chemical Properties

light yellow to yellow-brown crystalline solid

Uses

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

Uses

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

Definition

ChEBI: 1,4'-bipiperidine is a bipiperidine.

Synthesis

General procedure for the synthesis of 4-piperidinylpiperidine from hexahydropyridine and N-tert-butoxycarbonyl-4-piperidone: hexahydropyridine (1.549 g, 18.19 mmol), sodium triacetoxyborohydride (3.85 g, 19.2 mmol) and acetic acid (0.0910 g, 1.52 mmol) were added to a solution of 1-tert-butoxycarbonyl-4-piperidone (3.02 g , 15.2 mmol) in a solution of dichloromethane (25.0 mL). The reaction mixture was stirred at room temperature for 16 hours at 0 °C. Upon completion of the reaction, the reaction solution was cooled to 0 °C, the reaction was quenched by the addition of saturated aqueous sodium bicarbonate solution and extracted with dichloromethane. The organic layers were combined, dried with anhydrous sodium sulfate, filtered and the filtrate was concentrated under reduced pressure. The residue was dissolved in 1.0 N hydrochloric acid and extracted with ethyl acetate. The aqueous phase was alkalized with 48% aqueous sodium hydroxide and extracted again with dichloromethane. The organic layer was dried over anhydrous sodium sulfate, filtered and the filtrate was concentrated under reduced pressure. The residue was dissolved in methanol (25.0 mL), concentrated hydrochloric acid (5.0 mL) was added and stirred at 40°C for 12 hours. After the reaction solution was concentrated and dried, the residue was dissolved in distilled water, alkalized with 48% aqueous sodium hydroxide and extracted with dichloromethane. The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give 4-(piperidin-1-yl)piperidine (2.04 g, 12.1 mmol, 80% yield) as a white solid.

References

[1] Patent: TW2016/2093, 2016, A. Location in patent: Paragraph 0317

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