Pyridine → HCID 22729929, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-[1-Benzyl-4-(3-methoxy-phenyl)-piperidin-4-yl]-N-methyl-benzamide (1.01 g, 2.44 mmol), in CH2Cl2 (24 mL) was added pyridine (0.30 mL, 3.71 mmol). The reaction was cooled to −50° C. and triflic anhydride (0.45, 2.67 mmo) was added dropwise over 1 minutes. The reaction was stirred at −50° C. for 1.5 hours and at room temperature for 0.5 hours. The mixture was cooled to −50° C. and 2-amino-2-methyl propanol (0.36 mL, 3.77 mmol) was added. The reaction was allowed to warm to room temperature and stirred at room temperature for 16 hours. To the mixture was added water (5 mL) and the aqueous layer was extracted with CH2Cl2 (3×15 mL). The combined extracts were dried (MgSO4) and concentrated. Purification by flash chromatography with hexanes/EtOAc (1:1) afforded 0.75 g (68% yield) of 1-Benzyl-4-[4-(4,4-dimethyl-4,5-dihydro-oxazol-2-yl)-phenyl]-4-(3-methoxy-phenyl)-piperidine. 1HNMR (400 MHz, CDCl3) δ; 7.83 (d, 2H), 7.38-7.21 (comp, 7H), 7.18 (t, 1H), 6.81-6.75 (comp, 2H), 6.63 (d, 1H), 4.08 (s, 2H), 3.78 (s, 3H), 3.41 (s, 2H), 2.79-2.40 (comp, 8H), 1.38 (s, 3H); MS (M+1) 454.2.

Provenance & Evidence