1,4′-Bipiperidine

light yellow to yellow-brown crystalline solid

1,4'-bipiperidine is a bipiperidine.

Piperidine (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-piperidinone (3.02 g, 15.2 mmol) in dichloromethane (25.0 mL) at 0° C., and the resulting mixture was stirred at room temperature for 16 hours. The reaction liquid was cooled to 0° C. A saturated aqueous solution of sodium hydrogencarbonate was added to the reaction liquid, and the resulting mixture was extracted with dichloromethane. The organic layer was dried over anhydrous sodium sulfate and filtered, and the filtrate was concentrated under reduced pressure. The residue was dissolved in hydrochloric acid (1.0 N), and the resulting mixture was extracted with ethyl acetate. A 48percent aqueous solution of sodium hydroxide was added to the aqueous layer for basification, and then the resulting mixture was extracted with dichloromethane. The organic layer was dried over anhydrous sodium sulfate and filtered, and the filtrate was concentrated under reduced pressure. The residue was dissolved in methanol (25.0 mL), and concentrated hydrochloric acid (5.0 mL) was added, and then the resulting mixture was stirred at 40° C. for 12 hours. The reaction liquid was concentrated and exsiccated, and then the residue was dissolved in distilled water. A 48percent aqueous solution of sodium hydroxide was added for basification, and then the resulting mixture was extracted with dichloromethane. The organic layer was dried over anhydrous sodium sulfate and filtered, and the filtrate was concentrated under reduced pressure. 4-(Piperidin-1-yl)piperidine (2.04 g, 12.1 mmol, 80percent) was obtained as a white solid.Reference Example 19 Synthesis of 4-(piperidin-1-yl)piperidine (0391) (0392) Piperidine (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-piperidinone (3.02 g, 15.2 mmol) in dichloromethane (25.0 mL) at 0° C., and the resulting mixture was stirred at room temperature for 16 hours. The reaction liquid was cooled to 0° C. A saturated aqueous solution of sodium hydrogencarbonate was added to the reaction liquid, and the resulting mixture was extracted with dichloromethane. The organic layer was dried over anhydrous sodium sulfate and filtered, and the filtrate was concentrated under reduced pressure. The residue was dissolved in hydrochloric acid (1.0 N), and the resulting mixture was extracted with ethyl acetate. A 48percent aqueous solution of sodium hydroxide was added to the aqueous layer for basification, and then the resulting mixture was extracted with dichloromethane. The organic layer was dried over anhydrous sodium sulfate and filtered, and the filtrate was concentrated under reduced pressure. The residue was dissolved in methanol (25.0 mL), and concentrated hydrochloric acid (5.0 mL) was added, and then the resulting mixture was stirred at 40° C. for 12 hours. The reaction liquid was concentrated and exsiccated, and then the residue was dissolved in distilled water. A 48percent aqueous solution of sodium hydroxide was added for basification, and then the resulting mixture was extracted with dichloromethane. The organic layer was dried over anhydrous sodium sulfate and filtered, and the filtrate was concentrated under reduced pressure. 4-(Piperidin-1-yl)piperidine (2.04 g, 12.1 mmol, 80percent) was obtained as a white solid. (0393)

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

Molecular Weight:168.28
XLogP3:1.2
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:1
Exact Mass:168.162648646
Monoisotopic Mass:168.162648646
Topological Polar Surface Area:15.3
Heavy Atom Count:12
Complexity:124
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes