Piperidine-1-sulfonyl chloride → Piperidine-1-sulfonic acid [5-(2,4-dichloro-phenyl)-pyridin-2-yl]-amide

HRID 1510110Notes

Reaction equation

HRID 1510110 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[CH:10]=[CH:11][C:12]([NH2:15])=[N:13][CH:14]=1.[N:16]1([S:22](Cl)(=[O:24])=[O:23])[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1>N1C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[CH:10]=[CH:11][C:12]([NH:15][S:22]([N:16]2[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]2)(=[O:24])=[O:23])=[N:13][CH:14]=1

Participants

4

Reactant 2

HCID 11298344Piperidine-1-sulfonyl chlorideHCID 624923945-(2,4-Dichlorophenyl)pyridin-2-amine

Product 1

HCID 11717987Piperidine-1-sulfonic acid [5-(2,4-dichloro-phenyl)-pyridin-2-yl]-amideYield 67.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 0.23 g (1 mmol) of 5-(2,4-dichloro-phenyl)-pyridin-2-ylamine and 0.2 g (1.1 mmol) of piperidine-1-sulfonyl chloride (preparation: Bull. Soc. Chim. Fr.; 1936, p 2143) in pyridine (10 ml) was heated to reflux until completion of reaction according to HPLC analysis (20 h). After concentration in vacuo the residue was taken up in EtOAc, which was then washed with 1N aqueous HCl, saturated brine, dried over sodium sulphate and concentrated in vacuo. The residue was applied to a silica gel column with EtOAc/toluene (9/1 to 1/1) as eluent. Combination of the purified fractions and concentration in vacuo gave 0.26 g (67%) of the desired piperidine-1-sulfonic acid [5-(2,4-dichloro-phenyl)-pyridin-2-yl]-amide as a brown crystalline solid. ISN mass spectrum, m/e: 384 (M−1 calculated for C16H17Cl2N2O2S: 384).

Workup

  1. temperatureto reflux until completion of reaction
  2. customaccording to HPLC analysis (20 h)
  3. concentrationAfter concentration in vacuo the residue
  4. washwhich was then washed with 1N aqueous HCl, saturated brine
  5. dry with materialdried over sodium sulphate
  6. concentrationconcentrated in vacuo
  7. concentrationCombination of the purified fractions and concentration in vacuo

Sources & evidence

ORD record
ord-57b765f939d6415295eeb517b8b8dcf1
Source dataset
uspto-grants-2012_07
Patent number
US08211913B2

Reaction notes

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