3-(PIPERIDINE-1-SULFONYL)-BENZOICACID

To a stirred solution of 3-(chlorosulfonyl)benzoic acid (1.10 g, 5.00 mmol) in DCM (10 mL) was added piperidine (1.49 g, 17.5 mmol) at 0° C., and the resulting solution stirred for 30 minutes. The volatiles were then removed in vacuo and the residue treated with aqueous 1N KHSO4. The aqueous phase was then extracted with ethyl acetate (.x.3), and the combined organic phases dried over anhydrous magnesium sulfate, filtered and evaporated in vacuo to afford 3-(piperidin-1-ylsulfonyl)benzoic acid (1.22 g, 4.52 mmol, 90percent).1H NMR (d6 DMSO): 13.54 (1H, br), 8.24 (1H, dt, J 8.0 1.4 Hz), 8.18 (1H, t, J 1.8 Hz), 7.97 (1H, dt, J 8.0 1.6 Hz), 7.79 (1H, t, J 7.7 Hz), 2.93-2.88 (4H, m), 1.58-1.50 (4H, m), 1.40-1.32 (2H, m).To a stirred solution of 3-(chlorosulfonyl) benzoic acid (0.3 g, 1.36 mmol) in DCM (5 mL) was added piperidine (0.35 g, 0.4ml, 4.08 mmol) at 0° C, and the resulting solution was stirred for 2 hours. The volatiles were then evaporated under reduced pressure and the residue treated with aqueous IN KHSO4. The aqueous phase was then extracted with ethyl acetate (x3), and the combined organic phases dried over anhydrous magnesium sulfate, filtered and evaporated in vacuo to give 3-(piperidin-l-ylsulfonyl)benzoic acid as a white solid (0.34 g, 1.262 mmol, 90percent). NMR (400MHZ, CDCL3): 8.41 (1H, br), 8.26 (1H, dt, J= 8.0Hz , 1.4 - - Hz), 7.94 (1H, dt, J= 8.0Hz , 1.6 Hz), 7.61 (1H, t, J= 7.7 Hz), 2.98-2.96 (4H, m), 1.62-1.56 (4H, m), 1.40-1.34 (2H, m). To a stirred solution of 3-(chlorosulfonyl)benzoic acid (1.10 g, 5.00 mmol) in DCM (10 mL) was added piperidine (1.49 g, 17.5 mmol) at 00C, and the resulting solution stirred for 30 minutes. The volatiles were then removed in vacuo and the residue treated with aqueous IN KHSO4. The aqueous phase was then extracted with ethyl acetate (x3), and the combined organic phases dried over anhydrous magnesium sulfate, filtered and evaporated in vacuo to afford 3-(piperidin-l-ylsulfonyl)benzoic acid (1.22 g, 4.52 mmol, 90percent).1H NMR (d6 DMSO): 13.54 (IH, br), 8.24 (IH, dt, J 8.0 1.4 Hz), 8.18 (IH, t, J 1.8 Hz), 7.97 (IH, dt, J 8.0 1.6 Hz), 7.79 (IH, t, J 1.1 Hz), 2.93-2.88 (4H, m), 1.58-1.50 (4H, m), 1.40-1.32 (2H, m).

Molecular Weight:269.32
XLogP3:1.4
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:5
Rotatable Bond Count:3
Exact Mass:269.07217913
Monoisotopic Mass:269.07217913
Topological Polar Surface Area:83.1
Heavy Atom Count:18
Complexity:395
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes