Piperidine → 3-(Piperidine-1-sulfonyl)benzoic acid

HRID 1919855Notes

Reaction equation

HRID 1919855 reaction equation
Cl[S:2]([C:5]1[CH:6]=[C:7]([CH:11]=[CH:12][CH:13]=1)[C:8]([OH:10])=[O:9])(=[O:4])=[O:3].[NH:14]1[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1>C(Cl)Cl>[N:14]1([S:2]([C:5]2[CH:6]=[C:7]([CH:11]=[CH:12][CH:13]=2)[C:8]([OH:10])=[O:9])(=[O:4])=[O:3])[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1

Participants

4

Reactant 2

HCID 8082PiperidineHCID 77641Benzoic acid, 3-(chlorosulfonyl)-

Product 1

HCID 7678893-(Piperidine-1-sulfonyl)benzoic acidYield 90.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 3-(chlorosulfonyl)benzoic acid (1.10 g, 5.00 mmol) in DCM (10 mL) was added piperidine (1.49 g, 17.5 mmol) at 0° C., and the resulting solution stirred for 30 minutes. The volatiles were then removed in vacuo and the residue treated with aqueous 1N KHSO4. The aqueous phase was then extracted with ethyl acetate (×3), and the combined organic phases dried over anhydrous magnesium sulfate, filtered and evaporated in vacuo to afford 3-(piperidin-1-ylsulfonyl)benzoic acid (1.22 g, 4.52 mmol, 90%).

Workup

  1. customThe volatiles were then removed in vacuo
  2. additionthe residue treated with aqueous 1N KHSO4
  3. extractionThe aqueous phase was then extracted with ethyl acetate (×3)
  4. dry with materialthe combined organic phases dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-391a830bf78347ad88d2fef5341f9618
Source dataset
uspto-grants-2012_05
Patent number
US08168673B2

Reaction notes

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