1-acetyl-N-methoxy-N-methylpiperidine-4-carboxamide → 1,4-Diacetylpiperidine

Participants

Reaction Conditions

Reaction Steps

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.

Provenance & Evidence