Sodium Hydroxide → 3-Chloro-5-(3,5-dimethylpiperidinosulfonyl)benzoic Acid

HRID 355144Notes

Reaction equation

HRID 355144 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([S:11](Cl)(=[O:13])=[O:12])[CH:10]=1)[C:5]([OH:7])=[O:6].Cl.[CH3:16][CH:17]1[CH2:22][CH:21]([CH3:23])[CH2:20][NH:19][CH2:18]1.[OH-].[Na+]>O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([S:11]([N:19]2[CH2:20][CH:21]([CH3:23])[CH2:22][CH:17]([CH3:16])[CH2:18]2)(=[O:13])=[O:12])[CH:10]=1)[C:5]([OH:7])=[O:6]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 38612753-Chloro-5-(chlorosulfonyl)benzoic acidHCID 22670446HCID 22670446, compound

Product 1

HCID 205059493-Chloro-5-(3,5-dimethylpiperidinosulfonyl)benzoic Acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

3-Chloro-5-chlorosulfonylbenzoic acid (770 mg., 3 m moles) is added to a solution of 3,5-dimethylpiperidine hydrochloride in 30 ml. of water followed by the portionwise addition of 12 ml. of 1 N sodium hydroxide solution with stirring. After 1.5 hrs. at room temperature the reaction mixture is filtered and the filtrate acidified with 12 N hydrochloric acid. The product, 600 mg., m.p. 226°-231° C., is recrystallized from acetone-hexane, 390 mg., m.p. 232.5°-234° C.

Workup

  1. filtrationat room temperature the reaction mixture is filtered
  2. custom, m.p. 226°-231° C., is recrystallized from acetone-hexane, 390 mg

Sources & evidence

ORD record
ord-510b13a5dd614ad0a6f7c8f0a457c2bc
Source dataset
uspto-grants-1983_03
Patent number
US04377521

Reaction notes

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