Allyl bromide → 3-(3,4-Dimethoxyphenyl)-1-(prop-2-en-1-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].[CH2:17](Br)[CH:18]=[CH2:19]>CC(C)=O.[Ag]=O>[CH2:19]([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)[CH:18]=[CH2:17]Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 20 °C
Procedure
2.8 g of silver oxide were added to a solution of 5.6 g of 3-(3',4'-dimethoxyphenyl)-piperidine in 28 ml of acetone and then 2.3 ml of allyl bromide were added dropwise thereto with slow cooling. The mixture was stirred at 20° C for 30 minutes and was then 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 5.55 g of N-allyl-3-(3',4'-dimethoxyphenyl)-piperidine.
Workup
- filtrationwas then 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-9520700508b8411ca156d8943583fdae
- Source dataset
- uspto-grants-1978_02
- Patent number
- US04072685
Reaction notes
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