Nitromethane → 4-Hydroxy-4-nitromethyl-1-(4-pyridyl)piperidine
Reaction equation
[N+:1]([CH3:4])([O-:3])=[O:2].[Na].[N:6]1[CH:11]=[CH:10][C:9]([N:12]2[CH2:17][CH2:16][C:15](=[O:18])[CH2:14][CH2:13]2)=[CH:8][CH:7]=1>CO>[OH:18][C:15]1([CH2:4][N+:1]([O-:3])=[O:2])[CH2:14][CH2:13][N:12]([C:9]2[CH:8]=[CH:7][N:6]=[CH:11][CH:10]=2)[CH2:17][CH2:16]1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of nitromethane (2.31 ml) in methanol (5.4 ml) was added sodium (70 mg) at ice-cooled temperature. The resulting mixture was added dropwise to a solution of 1-(4-pyridyl)-4-piperidone (5.36 g) in methanol (10.7 ml) at ice-cooled temperature for 10 minutes, and stirred for 15 hours at room temperature. The precipitate was filtered, and washed with methanol to obtain the title compound (5.31 g).