Sodium Bicarbonate → rac-cis-N-((3-Methylpiperidin-2-yl)methyl)quinoline-8-carboxamide

Participants

Reaction Steps

Cerium ammonium nitrate (1.25 g, 2.28 mmol) was added portionwise to a mixture of rac-cis-N-((1-(4-methoxybenzyl)-3-methylpiperidin-2-yl)methyl)quinoline-8-carboxamide (0.23 g, 0.57 mmol) in acetone/water (10 mL, 9:1 v/v) at 0° C. and allowed to stir at rt for 5 h. Sat. NaHCO3 (aq.) was added and the resulting suspension was stirred at r.t for 10 min, concentrated in vacuo to remove the acetone, then filtered through diatomaceous earth and rinsed with EtOAc. The bi-layer filtrate was extracted with EtOAc and the combined organic layer was washed with brine, dried over MgSO4 and concentrated in vacuo to provide a brown oil as a 1:1 mixture of rac-cis-N-((3-methylpiperidin-2-yl)methyl)quinoline-8-carboxamide/4-methoxybenzaldehyde, which was used as-is without further purification. MS (ESI) 284.13 (M+H).

Provenance & Evidence