Benzene → 1-[3-(3,4-Dimethoxyphenyl)piperidin-1-yl]ethan-1-one
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].C1C=CC=CC=1.[C:23](OC(=O)C)(=[O:25])[CH3:24].C(=O)(O)[O-].[Na+]>O>[C:23]([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)(=[O:25])[CH3:24]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 20 °C
Procedure
A mixture of 8 g of 3-(3',4'-dimethoxyphenyl)-piperidine, 80 ml of benzene and 3.6 ml of acetic acid anhydride was stirred at 20° C for an hour and was then diluted with 100 ml of water. 500 ml of an aqueous solution saturated with sodium bicarbonate were added thereto and the mixture was stirred for an hour and then was decanted. The aqueous phase was re-extracted with ethyl acetate and the organic phases were washed with water, dried and evaporated to dryness. The residue was chromatographed over silica gel and was eluted with a 6-3-1 cyclohexane-chloroform-triethylamine mixture to obtain 6.75 g of N-acetyl-3-(3',4'-dimethoxyphenyl)-piperidine.
Workup
- stirringthe mixture was stirred for an hour
- customwas decanted
- extractionThe aqueous phase was re-extracted with ethyl acetate
- washthe organic phases were washed with water
- customdried
- customevaporated to dryness
- customThe residue was chromatographed over silica gel
- washwas eluted with a 6-3-1 cyclohexane-chloroform-triethylamine mixture
Sources & evidence
- ORD record
- ord-6f0d9fe2863b4bd78b212c160161ff3c
- Source dataset
- uspto-grants-1978_02
- Patent number
- US04072685
Reaction notes
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