tert-Butyl 4-(4-nitrobenzylidene)piperidine-1-carboxylate → 4-(4-Nitrobenzylidene)piperidine
Reaction equation
[N+:1]([C:4]1[CH:23]=[CH:22][C:7]([CH:8]=[C:9]2[CH2:14][CH2:13][N:12](C(OC(C)(C)C)=O)[CH2:11][CH2:10]2)=[CH:6][CH:5]=1)([O-:3])=[O:2]>ClCCl.FC(F)(F)C(O)=O>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([CH:8]=[C:9]2[CH2:10][CH2:11][NH:12][CH2:13][CH2:14]2)=[CH:22][CH:23]=1)([O-:3])=[O:2]Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Procedure
tert-Butyl 4-(4-nitrobenzylidene)piperidine-1-carboxylate (31.4 mmol, 10 g) was stirred in a mixture of dichloromethane/trifluoroacetic acid for 3 hours. The reaction was concentrated under reduced pressure and water was added. Solid sodium hydrogen carbonate was added portionwise until no further gas was evolved. The aqueous mixture was extracted with ethyl acetate. The organic phase was dried (magnesium sulfate), filtered and concentrated under reduced pressure to give the title compound (5.2 g). MS (ESI) m/z 219.1 [M+H]+