1-Iodopropane → Piperidine, 3-(3,4-dimethoxyphenyl)-1-propyl-
Reaction equation
[CH2:1](I)[CH2:2][CH3:3].[CH3:5][O:6][C:7]1[CH:8]=[C:9]([CH:15]2[CH2:20][CH2:19][CH2:18][NH:17][CH2:16]2)[CH:10]=[CH:11][C:12]=1[O:13][CH3:14]>C(Cl)(Cl)Cl.[Ag]=O>[CH2:1]([N:17]1[CH2:18][CH2:19][CH2:20][CH:15]([C:9]2[CH:10]=[CH:11][C:12]([O:13][CH3:14])=[C:7]([O:6][CH3:5])[CH:8]=2)[CH2:16]1)[CH2:2][CH3:3]Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 20 °C
Procedure
2 g of silver oxide and then 2 ml of propyl iodide were added to a solution of 4 g of 3-(3',4'-dimethoxyphenyl)-piperidine in 20 ml of chloroform and the mixture was stirred for 8 hours at 20° C under an inert atmosphere. Another 1 g of silver oxide and 1 ml of propyl iodide were added and the mixture was stirred for 15 hours. The mixture was filtered and the filtrate was evaporated to dryness. The residue was chromatographed over silica gel and eluted with a 6-3-1 cyclohexane-chloroform-triethylamine mixture to obtain 3.2 g of N-propyl-3-(3',4'-dimethoxyphenyl)-piperidine.
Workup
- stirringthe mixture was stirred for 15 hours
- filtrationThe mixture was filtered
- customthe filtrate was evaporated to dryness
- customThe residue was chromatographed over silica gel
- washeluted with a 6-3-1 cyclohexane-chloroform-triethylamine mixture
Sources & evidence
- ORD record
- ord-ace686240db543af8e6e1562059e4202
- Source dataset
- uspto-grants-1978_02
- Patent number
- US04072685
Reaction notes
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