ChemicalBook CAS DataBase List 4-Piperidinopiperidine

4-Piperidinopiperidine synthesis

5synthesis methods

Product Name:4-Piperidinopiperidine
CAS Number:4897-50-1
Molecular formula:C10H20N2
Molecular Weight:168.28

110-89-4

79099-07-3

4897-50-1

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.

110-89-4
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79099-07-3 Synthesis

79099-07-3
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$5.00/5g

4897-50-1
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$19.00/5g

Yield:4897-50-1 80%

Reaction Conditions:

with sodium tris(acetoxy)borohydride;acetic acid in dichloromethane at 0 - 20; for 16 h;

Steps:

19 Synthesis of 4-(piperidin-1-yl)piperidine

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 48% 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 48% 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, 80%) was obtained as a white solid.

References:

TW2016/2093,2016,A Location in patent:Paragraph 0317