Sodium Hydroxide → 1-Benzyl-4-methyl-4-phenylpiperidine
Reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]([CH3:15])(O)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Al+3].[Cl-].[Cl-].[Cl-].[OH-].[Na+]>C1C=CC=CC=1>[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]([CH3:15])([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
1-Benzyl-4-methylpiperidin-4-ol (4.81 g, 23.4 mmol) was added to a suspension of AlCl3 (15.62 g, 117 mmol) in benzene (100 mL) at room temperature under argon. The mixture was stirred at reflux for 24 hours, then cooled and poured cautiously into ice water (100 g of ice, 50 mL of water). The aqueous phase was adjusted to pH 11-12 by addition of 6 N aqueous NaOH at 0° C., and extracted with EtOAc (3×100 mL). The combined organic solutions were dried over magnesium sulfate and concentrated. The residue was chromatographed (hexane-Et2O 19/1 to 9/1, followed by hexane-EtOAc 3/1), giving the desired product (3.23 g, 52%) as a brown oil: 1H NMR δ 1.25 (s, 3 H), 1.80 (m, 2 H), 2.17 (m, 2 H), 2.44 (m, 2 H), 2.55 (m, 2 H), 3.50 (s, 2 H), 7.25 (m, 1 H), 7.35 (m, 4 H); 13C NMR δ 36.82, 37.65, 50.95, 54.93, 64.08, 126.19, 126.51, 127.59, 128.83, 128.95, 129.05, 129.89, 139.24.
Workup
- temperatureat reflux for 24 hours
- temperaturecooled
- extractionextracted with EtOAc (3×100 mL)
- dry with materialThe combined organic solutions were dried over magnesium sulfate
- concentrationconcentrated
- customThe residue was chromatographed (hexane-Et2O 19/1 to 9/1, followed by hexane-EtOAc 3/1)
Sources & evidence
- ORD record
- ord-66e81472bfab4753a407f901dc3b55f8
- Source dataset
- uspto-grants-2004_04
- Patent number
- US06720324B2
Reaction notes
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