Thionyl Chloride → (4-(Chloromethyl)phenyl)(piperidin-1-yl)methanone
Reaction equation
O[CH2:2][C:3]1[CH:16]=[CH:15][C:6]([C:7]([N:9]2[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]2)=[O:8])=[CH:5][CH:4]=1.S(Cl)([Cl:19])=O>C(Cl)(Cl)Cl>[Cl:19][CH2:2][C:3]1[CH:16]=[CH:15][C:6]([C:7]([N:9]2[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]2)=[O:8])=[CH:5][CH:4]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
The alcohol (6.97 mmol) of the preceding paragraph was dissolved in 15 mL CHCl3, followed by the addition of 0.66 mL thionyl chloride. The solution was refluxed for 1 hour and then allowed to stand at room temperature overnight. The volume was then reduced by 50% on a rotary evaporator and the solution was diluted with CCl4 and petroleum ether to induce crystallization. The product 1-(4'-chloromethylbenzoyl)piperidine was isolated in 92% yield and had a melting point of 106°-108° C.