1-CHLOROCARBONYL-4-PIPERIDINOPIPERIDINE Chemical Properties

Melting point:

60-64°C

Boiling point:

344.5±31.0 °C(Predicted)

Density 

1.184±0.06 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

solubility 

Acetonitrile (Slightly), Chloroform (Slightly, Heated)

form 

Solid

pka

9.19±0.20(Predicted)

color 

Off-White to Light Beige

Stability:

Moisture Sensitive

Safety Information

Hazard Codes 

C

Risk Statements 

34

Safety Statements 

26-27-36/37/39-45

RIDADR 

UN 3261 8 / PGIII

WGK Germany 

3

1-CHLOROCARBONYL-4-PIPERIDINOPIPERIDINE Usage And Synthesis

Uses

Reactant for synthesis of:

• Macrocyclic ureas as selective Chk1 inhibitors
• Etoposide prodrug for dual prodrug-enzyme antitumor therapy
• Phosphodiesterase 4 inhibitors
• Camptothecin analogs

Synthesis

The general procedure for the synthesis of piperidinyl piperidine carbonyl chloride from 4-piperidinyl piperidine and triphosgene is as follows: Example 1 Synthesis of [1,4']bipiperidine-1'-carbonyl chloride (II): triphosgene (16.48 g) was dissolved in methylene chloride (200 ml), and methylene chloride solution of 4-piperidinyl piperidine (20 g) (200 ml) was slowly added, and the temperature of the reaction was maintained at 20 to 25 °C and the reaction time was 1-2 hours. During this process, dichloromethane was removed by distillation and acetonitrile was added subsequently. Distillation was continued to remove dichloromethane and acetonitrile until the reaction temperature was raised to 70°C. Fresh dichloromethane was added to the reaction mixture and after forming a homogeneous slurry, potassium carbonate (30-35 g) was added and the reaction mixture was stirred for 1-2 hours. After completion of the reaction, the reaction mixture was filtered and the filtrate was concentrated. Hexane was slowly added to the concentrate under stirring to precipitate a solid product. The solid was collected by filtration, washed with hexane and dried under reduced pressure at about 40 °C to give 27 g of product (98.5% yield). The product was analyzed by GC showing a purity of 99.80% and no dimer impurities were detected.

References

[1] Patent: US2011/144342, 2011, A1. Location in patent: Page/Page column 7
[2] Patent: EP2341046, 2011, A2. Location in patent: Page/Page column 9
[3] Patent: US2007/208050, 2007, A1. Location in patent: Page/Page column 7
[4] Patent: WO2009/97695, 2009, A1. Location in patent: Page/Page column 114-115
[5] Patent: WO2006/16203, 2006, A1. Location in patent: Page/Page column 8-9

1-CHLOROCARBONYL-4-PIPERIDINOPIPERIDINE(103816-19-9)Related Product Information

• 1-benzyl-4-(piperidin-1-yl)-1,2,3,6-tetrahydropyridine
• 12-ethyl-8-methyl-9-oxo-7-propionyl-9,11-dihydroindolizino[1,2-b]quinolin-2-yl [1,4'-bipiperidine]-1'-carboxylate
• [1,4'-Bipiperidine]-1'-carboxylic acid
• Irinotecan Hydroxyl Acid
• Irinotecan Lactone IMpurity
• Irinotecan Impurity 26
• Irinotecan Impurity 18
• Irinotecan IMpurity G
• 11-Desethyl Irinotecan
• Irinotecan Impurity 3
• Irinotecan Impurity 8
• Irinotecan Impurity 29
• 1-Chlorocarbonyl-4-piperidinopiperidine hydrochloride
• Dimethylcarbamoyl chloride
• Diethylcarbamyl chloride
• N-CHLOROMETHYL PIPERIDINE
• 1-PIPERIDINECARBONYL CHLORIDE
• 1-CHLOROCARBONYL-4-PIPERIDINOPIPERIDINE