Piperidine → 2,4-Dichloro-5-(piperidin-1-ylsulfonyl)benzoic acid

Reaction equation

[NH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[Cl:7][C:8]1[CH:16]=[C:15]([Cl:17])[C:14]([S:18](Cl)(=[O:20])=[O:19])=[CH:13][C:9]=1[C:10]([OH:12])=[O:11].[OH-].[Na+]>O>[Cl:7][C:8]1[CH:16]=[C:15]([Cl:17])[C:14]([S:18]([N:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)(=[O:20])=[O:19])=[CH:13][C:9]=1[C:10]([OH:12])=[O:11]

Participants

Procedure

A stirred suspension of 1.7 g. (0.02 mole) of piperidine and 5.8 g. (0.02 mole) of 2,4-dichloro-5-chlorosulfonylbenzoic acid (Sturm, et al., Ber., 99, 328 (1966) in 70 ml. of water and cooled to 15° C. is treated dropwise with 50 ml. of 1N sodium hydroxide. When the addition is complete, the mixture is allowed to warm to room temperature and remain for 1 hr. The hazy suspension is filtered and the clear filtrate acidified with 12N hydrochloric acid. The precipitated solids are filtered and dried, 7.7 g., m.p. 200°-205° C. A sample is recrystallized from acetonitrile, m.p. 205°-206° C.