1-Benzyl-3,3-dimethylpiperidin-4-amine → 3,3-Dimethylpiperidin-4-amine
Reaction equation
[NH2:1][CH:2]1[CH2:7][CH2:6][N:5](CC2C=CC=CC=2)[CH2:4][C:3]1([CH3:16])[CH3:15]>CO.[H][H].[OH-].[OH-].[Pd+2]>[NH2:1][CH:2]1[CH2:7][CH2:6][NH:5][CH2:4][C:3]1([CH3:16])[CH3:15]Participants
5
Reactant 1
Product 1
Reagents, catalysts & solvents 3
Procedure
A mixture of 20% Pd(OH)2 on carbon (0.3 g) and 4-amino-1-benzyl-3,3-dimethylpiperidine (1.6 g, 7.33 mmol) in methanol (25 ml) was stirred in hydrogen atmosphere (1 atm.) at 30° C. for 6 hr. The catalyst was filtered off, washed with methanol and filtrate was concentrated to dryness to afford 4-amino-3,3-dimethylpiperidine. Yield 0.7 g (75%), C7H16N2, m/z 129 (M+1), PMR (CDCl3): 0.9 (s, 6H), 1.5 (m, 2H), 1.58 (bs, 2H, D2O exchangeable), 2.26-2.68 (m, 4H), 3.06 (m, 1H), 3.52 (bs, 1H, D2O exchangeable).
Workup
- filtrationThe catalyst was filtered off
- washwashed with methanol and filtrate
- concentrationwas concentrated to dryness
Sources & evidence
- ORD record
- ord-a35043372c134177b158e7339a6f229b
- Source dataset
- uspto-grants-2005_11
- Patent number
- US06964966B2
Reaction notes
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