Water → Ethyl 4-(piperidin-1-yl)benzoate
Reaction equation
F[C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][CH:3]=1.[NH:13]1[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1.O>C(#N)C>[N:13]1([C:2]2[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][CH:3]=2)[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
Reaction of ethyl 4-fluorobenzoate with piperidine (3 equivalents) in acetonitrile was carried out at reflux for 4 days. Dilution of the cooled reaction mixture with several volumes of water provided a precipitate, which was filtered to provide ethyl 4-(piperidin-1-yl)benzoate. Reduction of the ester with lithium aluminum hydride (2 equivalents) in tetrahydrofuran gave the corresponding alcohol (Examples 71, 72).