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

HRID 1703719Notes

Reaction equation

HRID 1703719 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 1N sodium hydroxide solution with stirring. After 1.5 hrs. at room temperature the reaction mixture is filtered and the filtrate acidified with 12N 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-44e09f6f310446cb8495bba179a3ed14
Source dataset
uspto-grants-1978_11
Patent number
US04124590

Reaction notes

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