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

HRID 355139Notes

Reaction equation

HRID 355139 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 1 N 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 12 N 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-cf3ff938aae44ac8b4e798dc96cc6a6d
Source dataset
uspto-grants-1983_03
Patent number
US04377521

Reaction notes

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