ChemicalBook CAS DataBase List 1-[4-(2,4-DIFLUORO-BENZOYL)-PIPERIDIN-1-YL]-ETHANONE

1-[4-(2,4-DIFLUORO-BENZOYL)-PIPERIDIN-1-YL]-ETHANONE synthesis

8synthesis methods

Product Name:1-[4-(2,4-DIFLUORO-BENZOYL)-PIPERIDIN-1-YL]-ETHANONE
CAS Number:25519-77-1
Molecular formula:C14H16FNO2
Molecular Weight:249.28

462-06-6
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$10.00/5g

25503-90-6
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$5.00/1g

1-[4-(2,4-DIFLUORO-BENZOYL)-PIPERIDIN-1-YL]-ETHANONE

25519-77-1
19 suppliers
$446.00/25g

Yield: 60%

Reaction Conditions:

Stage #1:1-acetyl-piperidine-4-carboxylic acid with thionyl chloride in 1,2-dichloro-ethane at 20; for 1 h;
Stage #2:fluorobenzene with aluminum (III) chloride in 1,2-dichloro-ethane at 80; for 3 h;

Steps:

10
Intermediate 10: (4-fluoro-phenyl) -piperidin-4-yl-methanone (10)6.4g (49.5mmol) of isonipecotic acid are placed in the presence of 40ml of acetic anhydride. The reaction medium is heated to 130⁰C for 5h and then dry concentrated. After triturating with petroleum ether, the formed crystals are filtered. 7.79g of solid are obtained (92%) . 0.5g (2.92mmol) of the obtained solid are placed in ImL of 1,2- dichloroethane in the presence of 0.92mL (12.56mmol) of thionyl chloride, and this solution is then stirred for Ih at room temperature. The medium is dry concentrated and then the residue is taken up with 2mL of 1,2- dichloroethane . This solution is added to a mixture of 0.9Og (6.72 mmol) of AlCl₃ and 1.29mL (13.73 mmol) of fluorobenzene in ImL of 1, 2-dichloroethane . The reaction medium is heated to 80⁰C for 3h. After the solution has returned to room temperature, it is poured on ice water, then the medium is extracted with dichloromethane . After drying on MgSO₄, the organic phases are dry concentrated, the obtained residue is purified by flash chromatography on silica (CH₂Cl₂-MeOH: 95-5) . 0.44 g of an oil are isolated(60%) . TLC silica gel 60 F 254 Merck, CH₂Cl₂-MeOH: 95-5,Rf=O .38. The obtained oil is placed in 6mL of 6N hydrochloric acid and the mixture is heated to 100⁰C for18h. The medium is neutralized by adding a concentrated soda solution and extracted with ethyl acetate. After drying on MgSO₄, the organic phases are dry concentrated. 0.23 g of intermediate 10 are obtained as an oil (62%) . TLC silica gel 60 F 254 Merck, CH₂Cl₂-MeOH: 95-5, Rf=O.13.