ChemicalBook CAS DataBase List 1-pyridin-2-ylpiperidin-4-one

1-pyridin-2-ylpiperidin-4-one synthesis

5synthesis methods

Product Name:1-pyridin-2-ylpiperidin-4-one
CAS Number:264608-41-5
Molecular formula:C10H12N2O
Molecular Weight:176.22

8-(2-Pyridinyl)-1,4-dioxa-8-azaspiro[4.5]decane

264608-40-4
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264608-41-5
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Yield:264608-41-5 85%

Reaction Conditions:

with hydrogenchloride in tetrahydrofuran;water at 0 - 20; for 8 h;

Steps:

Step 3: Synthesis of 4-piperidone derivatives 19i-n

General procedure: To a solutionof N-heteroaryl-4-piperidone ethylene ketal (16ae or 16g)(1.20 mmol) in tetrahydrofuran (5 mL) was added 2 N hydrochloricacid solution (9 mL) dropwise at 0 C. After the addition wascomplete, the resulting mixture was stirred at room temperaturefor 8 h. Then aqueous saturated sodium hydrogen carbonate solutionwas added thereto, followed by extraction with ethyl acetate.The organic layer was washed with brine, dried over anhydroussodium sulfate, and concentrated in vacuum. The resulting residuewas purified by silica gel chromatography (dichloromethane/methanol, v/v, 99:1 to 95:5) to give the desired product. 1-(Pyridin-2-yl)piperidin-4-one (19i). This title compound wasprepared from 16a following step 3 of general procedure B. Yellowoil (85%). 1H NMR (300 MHz, CDCl3) d 8.40e8.35 (m, 1H), 8.14 (dd,J 4.2, 1.4 Hz, 1H), 7.25e7.18 (m, 2H), 3.64 (t, J 6.1 Hz, 4H), 2.58 (t,J 6.1 Hz, 4H).

References:

Wang, Zhengyu;Shi, Xiaofan;Zhang, Huan;Yu, Liang;Cheng, Yanhua;Zhang, Hefeng;Zhang, Huibin;Zhou, Jinpei;Chen, Jing;Shen, Xu;Duan, Wenhu [European Journal of Medicinal Chemistry,2017,vol. 139,p. 128 - 152]