1-acetyl-N-methoxy-N-methylpiperidine-4-carboxamide → 1,4-Diacetylpiperidine
Reaction equation
[C:1]([N:4]1[CH2:9][CH2:8][CH:7]([C:10](N(OC)C)=[O:11])[CH2:6][CH2:5]1)(=[O:3])[CH3:2].[CH3:16][Mg]Br>O1CCCC1>[N:4]1([C:1](=[O:3])[CH3:2])[CH2:5][CH2:6][CH:7]([C:10](=[O:11])[CH3:16])[CH2:8][CH2:9]1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
1-Acetyl-N-methoxy-N-methylpiperidine-4-carboxamide (59.10 g, 275.8 mmol) was dissolved in tetrahydrofuran (800 ml) and cooled to 0° C. Methylmagnesium bromide (110.3 ml, 331.0 mmol) (3.0 M in diethyl ether) was added slowly and the resulting white slurry was agitated for 1 hour. The reaction was quenched with 300 ml of 2M HCl and organic solvent was evaporated. The resulting aqueous slurry was extracted three times with 20:80 isopropanol/chloroform. The resulting extracts were washed with brine and evaporated to produce the desired product (38.40 g, 82.27% yield) as amber oil.
Workup
- customThe reaction was quenched with 300 ml of 2M HCl and organic solvent
- customwas evaporated
- extractionThe resulting aqueous slurry was extracted three times with 20:80 isopropanol/chloroform
- washThe resulting extracts were washed with brine
- customevaporated
Sources & evidence
- ORD record
- ord-da20895bae894ced9f8f891ae58cebd5
- Source dataset
- uspto-grants-2011_09
- Patent number
- US08022222B2
Reaction notes
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