Acetic Acid → N-(2-Cyano-4-fluorophenyl)-4-piperidone
Reaction equation
C1O[C:5]2([CH2:10][CH2:9][N:8]([C:11]3[CH:16]=[CH:15][C:14]([F:17])=[CH:13][C:12]=3[C:18]#[N:19])[CH2:7][CH2:6]2)[O:4]C1C.C(O)(=O)C>Cl>[C:18]([C:12]1[CH:13]=[C:14]([F:17])[CH:15]=[CH:16][C:11]=1[N:8]1[CH2:9][CH2:10][C:5](=[O:4])[CH2:6][CH2:7]1)#[N:19]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of 39 (1.483 g, 5.36 mmol) in 6N aqueous HCl (25 mL) was treated with acetic acid (50 mL) at room temperature. The mixture was stirred at room temperature (3 d). The solvent was removed in vacuo and the residue dissolved in dichloromethane and sodium carbonate solution. The aqueous layer was extracted with three additional portions of dichloromethane and the combined organic extracts were washed with brine, dried over Na2SO4, and concentrated under reduced pressure. PCTLC (SiO2, 6 mm, 20% EtOAc-80% hexane) afforded the title compound (40).