Water → 1-benzyl-N,4-dimethylpiperidin-3-amine
Reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([N:14]1[CH2:19][CH2:18][CH:17]([CH3:20])[CH:16]([NH:21][C:22](=O)OC)[CH2:15]1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.O>O1CCCC1>[CH2:7]([N:14]1[CH2:19][CH2:18][CH:17]([CH3:20])[CH:16]([NH:21][CH3:22])[CH2:15]1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
At about 0° C., lithium aluminum hydride (3.6 g, 92.8 mmol, 5.00 equiv.) was added in several batches to a solution of methyl 1-benzyl-4-methylpiperidin-3-yl-carbamate (5.0 g, 18.1 mmol, 1.00 equiv.) in tetrahydrofuran (100 mL). The resulting solution was heated at reflux for about 16 hours, and then water (10 mL) was added. The mixture was filtered, and the resulting filtrate was concentrated in vacuo to give a crude residue that was then purified by silica gel column chromatography (dichloromethane/methanol (20:1)) to afford the title product as a yellow oil (3.0 g; yield=72%). 1H NMR (300 MHz, CDCl3) δ: 7.20-7.38 (m, 5H), 3.58 (d, J=13.2 Hz, 1H), 3.48 (d, J=13.2 Hz, 1H), 2.60-2.82 (m, 2H), 2.46 (br s, 1H), 2.34 (s, 3H), 2.02-2.22 (m, 2H), 2.64-2.84 (m, 2H), 1.45-1.58 (m, 2H), 0.97 (d, J=6.9 Hz, 3H). LC-MS: m/z=219 (M+H)+.
Workup
- temperatureThe resulting solution was heated
- temperatureat reflux for about 16 hours
- filtrationThe mixture was filtered
- concentrationthe resulting filtrate was concentrated in vacuo
- customto give a crude residue that
- customwas then purified by silica gel column chromatography (dichloromethane/methanol (20:1))
Sources & evidence
- ORD record
- ord-218cb77e9eb749d0a1a155b9ffa1c669
- Source dataset
- uspto-grants-2012_10
- Patent number
- US08299084B2
Reaction notes
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