Isopropyl iodide → 3-(3,4-Dimethoxyphenyl)-1-(propan-2-yl)piperidine
Reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]2[CH2:16][CH2:15][CH2:14][NH:13][CH2:12]2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[CH:17](I)([CH3:19])[CH3:18]>CC(C)=O.[Ag]=O>[CH:17]([N:13]1[CH2:14][CH2:15][CH2:16][CH:11]([C:5]2[CH:6]=[CH:7][C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=2)[CH2:12]1)([CH3:19])[CH3:18]Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 20 °C
Procedure
2.5 g of silver oxide were added to a solution of 5 g of 3-(3',4'-dimethoxyphenyl)-piperidine in 25 ml of acetone and then 2.5 ml of isopropyl iodide were added dropwise. The mixture was stirred at 20° C for 24 hours and was filtered. The filtrate was evaporated to dryness and the residue was chromatographed over silica gel. Elution with a 6-3-1 cyclohexane-chloroform-triethylamine mixture yielded 4.8 g of N-isopropyl-3-(3',4'-dimethoxyphenyl)-piperidine.
Workup
- filtrationwas filtered
- customThe filtrate was evaporated to dryness
- customthe residue was chromatographed over silica gel
- washElution with a 6-3-1 cyclohexane-chloroform-triethylamine mixture
Sources & evidence
- ORD record
- ord-93bd034bfa1240d79f301e0de4324e48
- Source dataset
- uspto-grants-1978_02
- Patent number
- US04072685
Reaction notes
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