Hydrochloric Acid → 6-(2,6-Dimethoxyphenyl)-4,4-dimethylpiperidin-2-one

Participants

Reaction Conditions

Reaction Steps

A sealed tube containing a mixture of methyl 5-(2,6-dimethoxyphenyl)-3,3-dimethyl-5-oxopentanoate (474 mg; 1.61 mmol), ammonium acetate (1.241 g; 16.10 mmol), and NaBH3CN (106 mg; 1.61 mmol) in anh. MeOH (8 ml) was heated to 80° C. for 48 h. After cooling to rt, 2 M aq. HCl (7.5 ml) was added, and the volatiles were removed under reduced pressure. The resulting aq. layer was extracted with DCM (3×20 ml), and the mixed organic layers were dried over anh. MgSO4, filtered, and concentrated to dryness under reduced pressure. Purification by FC (DCM/MeOH=25/1) afforded 6-(2,6-dimethoxyphenyl)-4,4-dimethylpiperidin-2-one as a yellow solid. LC-MS (conditions D): tR=0.91 min.; [M+H]+: 264.22 g/mol.

Provenance & Evidence