Piperidine → Ethyl 4-(3-Piperidin-1-ylpropoxy)benzoate

Participants

Reaction Steps

A stirred mixture of ethyl 4-(3-chloropropoxy)benzoate (4.73 g) (D. A. Walsh et al J. Med. Chem. 1989, 32(1), 105), piperidine (2.9 ml), sodium carbonate (3.1 g) and potassium iodide (162 mg) in 1-butanol (50 ml) was heated at 105° C. for 16 h. The reaction was cooled to rt, diluted with EtOAc (100 ml), washed with water (3×50 ml), saturated brine (50 ml), dried (MgSO4) and evaporated to give the title compound (D1) (6.88 g). MS electrospray (+ion) 292 (MH+). 1H NMR δ (CDCl3): 7.98 (2H, d, J=8.8 Hz), 6.90 (2H, d, J=8.8 Hz), 4.34 (2H, q, J=7.5 Hz), 4.06 (2H, t, J=6.3 Hz), 2.46 (4H, m), 2.00 (2H, m), 1.50 (6H, m), 1.38 (3H, t, J=7.5 Hz).

Provenance & Evidence