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

HRID 1730602Notes

Reaction equation

HRID 1730602 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

5

Reactant 3

HCID 8082PiperidineHCID 14798Sodium HydroxideHCID 773362,4-Dichloro-5-(chlorosulphonyl)benzoic acid

Product 1

HCID 7679092,4-Dichloro-5-(piperidin-1-ylsulfonyl)benzoic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

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 acidifiedwith 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.

Workup

  1. additionA stirred suspension of 1.7 g
  2. additionis treated dropwise with 50 ml
  3. additionWhen the addition
  4. filtrationThe hazy suspension is filtered
  5. filtrationThe precipitated solids are filtered
  6. customdried
  7. customA sample is recrystallized from acetonitrile, m.p. 205°-206° C.

Sources & evidence

ORD record
ord-4031eb4ef1ef4b04a422eec5852d2bfc
Source dataset
uspto-grants-1976_11
Patent number
US03992441

Reaction notes

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