Ammonia → Ammonia
Reaction equation
[NH3:1].[C:2]([N:5]1[CH2:10][CH2:9][CH2:8][CH2:7][C:6]1=O)(=[O:4])[CH3:3]>CO.[OH-].[Pd+2].[OH-]>[NH3:5].[C:2]([N:5]1[CH2:10][CH2:9][CH:8]([NH2:1])[CH2:7][CH2:6]1)(=[O:4])[CH3:3]Participants
6
[NH3:1].[C:2]([N:5]1[CH2:10][CH2:9][CH2:8][CH2:7][C:6]1=O)(=[O:4])[CH3:3]>CO.[OH-].[Pd+2].[OH-]>[NH3:5].[C:2]([N:5]1[CH2:10][CH2:9][CH:8]([NH2:1])[CH2:7][CH2:6]1)(=[O:4])[CH3:3]0.88 Ammonia (85 ml) was added to a solution of N-acetylpiperidone (15 g, 106 mmol) in methanol (120 ml), followed by palladium hydroxide (2 g) and the mixture hydrogenated at room temperature and 60 psi for 18 hours. The reaction mixture was filtered through Arbocel®, the filtrate concentrated under reduced pressure and the residue azeotroped with toluene to give a yellow oil. The crude product was purified by column chromatography on silica gel using an elution gradient of dichloromethane:methanol:0.88 ammonia (96:3.5:0.5 to 84:14:2) to afford the title compound as a clear oil, 9.6 g.
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