Yield:-

Reaction Conditions:

with sodium hydroxide in chloroform;water;

Steps:

1 2-Chloro-5-(cis-3,5-dimethylpiperidinosulfonyl)benzoic Acid

2-Chloro-5-(cis-3,5-dimethylpiperidinosulfonyl)benzoic Acid 2-Chloro-5-chlorosulfonylbenzoic acid (510.2 g.) and cis-3,5-dimethylpiperidine hydrochloride are slurried in 7.0 l. of water and stirred at 15° C. as a cold solution of 240.0 g. of sodium hydroxide in 6 l. of water is added in a steady stream. The hazy reaction mixture is stirred at 20°-25° C. for 1 hour and then filtered by suction through a funnel precoated with diatomaceous earth filter aid. The filtrate is acidified with concentrated hydrochloric acid and the resulting precipitate collected. The cake is washed with methanol and ether, and air-dried to obtain 650.0 g. of crude product. This is dissolved in 6 l. of 1:1 isopropyl alcohol:chloroform and filtered. The filtrate is concentrated in vacuo to about 3 l. and the crystalline material filtered off. The filter cake is washed with isopropyl alcohol and ether. Air drying gives 471.0 g. of crystalline product, m.p. 250°-251° C. Anal. Calc'd for C₁₄ H₁₈ O₄ NSCl: C, 50.67; H, 5.47; N, 4.22. Found: C, 50.73; H, 5.46; N, 4.24.

References:

US3992441,1976,A