Piperidin-4-ol → 2-(4-Hydroxypiperidin-1-yl)-5-nitrobenzonitrile
Reaction equation
Cl[C:2]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][C:3]=1[C:4]#[N:5].[OH:13][CH:14]1[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1>C(O)C>[N+:10]([C:7]1[CH:8]=[CH:9][C:2]([N:17]2[CH2:18][CH2:19][CH:14]([OH:13])[CH2:15][CH2:16]2)=[C:3]([CH:6]=1)[C:4]#[N:5])([O-:12])=[O:11]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
2-chloro-5-nitrobenzonitrile (36 g) and 4-hydroxypiperidine (50 g) were added to ethanol (300 ml), and the mixture was stirred at a refluxing temperature for 1 h. The solvent was evaporated under reduced pressure. Diisopropyl ether was added to the residue to allow crystallization. The crystals were recrystallized from hydrous ethanol to give 5-nitro-2-(4-hydroxypiperidin-1-yl)benzonitrile (37.4 g), melting point: 114–115° C.