Fluorobenzene → 1-Acetyl-4-(4-fluorobenzoyl)piperidine

反応式

[Cl-].[Al+3].[Cl-].[Cl-].[F:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[C:12]([N:15]1[CH2:23][CH2:22][CH:18]([C:19](Cl)=[O:20])[CH2:17][CH2:16]1)(=[O:14])[CH3:13]>>[C:12]([N:15]1[CH2:16][CH2:17][CH:18]([C:19](=[O:20])[C:9]2[CH:10]=[CH:11][C:6]([F:5])=[CH:7][CH:8]=2)[CH2:22][CH2:23]1)(=[O:14])[CH3:13]

参加物

反応物 3

HCID 10008Fluorobenzene

HCID 1009501-Acetylpiperidine-4-carbonyl chloride

HCID 6451240Aluminum(III) Chloride

生成物 1

HCID 1172571-Acetyl-4-(4-fluorobenzoyl)piperidine収率 80%

実験手順

A mixture of 93 g. (0.7 mole) of aluminum chloride in 150 ml. of fluorobenzene was stirred while 70 g. (0.37 mole) of 1-acetylisonipecotic acid chloride was added in small portions. After the addition was complete, the mixture was refluxed for one hour. The mixture was poured onto ice and the two layers separated. The aqueous layer was extracted twice with chloroform and the chloroform extracts were added to the organic layer. The organic solution was dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated and 73.7 g. (80%) of 1-acetyl-4-(p-fluorobenzoyl)piperidine was obtained as a crystalline residue. Recrystallization from ligroin-isopropyl ether gave a white crystalline product melting at 75°-78° C.