Réaction #307052

Équation de réaction

5-bromo-2-fluorobenzaldehyde

2-methylpiperidine

sodium carbonate

→

title compound

Rendement 89.0%

5-bromo-2-(2-methylpiperidin-1-yl)benzaldehyde

Rendement 89.0%

Solvants

DMSO

water

Conditions de réaction

Traitement

1. 1
   Températureto cool to RT
2. 2
   AutreReaction mixture
3. 3
   Autrewas partitioned between H2O (1 L) and Et2O (2×750 mL)
4. 4
   Lavagethe combined organic layers were washed with brine (500 mL, pH 5-6 adjusted with HCl)
5. 5
   Séchagedried over MgSO4
6. 6
   Filtrationfiltered
7. 7
   Autredried under vacuum

Mode opératoire

To a solution of 5-bromo-2-fluorobenzaldehyde (13.20 g; 65.02 mmol) in DMSO (160 mL) and water (40 mL) were added 2-methylpiperidine (15.35 mL; 130.04 mmol) and anhydrous sodium carbonate (13.78 g; 130.04 mmol). The resulting mixture was heated at 120° C. for 16 h after which it was allowed to cool to RT. Reaction mixture was partitioned between H2O (1 L) and Et2O (2×750 mL) and the combined organic layers were washed with brine (500 mL, pH 5-6 adjusted with HCl), dried over MgSO4, filtered and dried under vacuum to give the title compound as a brown yellow oil (16.3 g, 89%). LC/MS (Method B): 282.1 (M+H)+. HPLC (Method A): Rt 2.20 min (Purity: 93.7%).

Source