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

HRID 490671Notes

Reaction equation

HRID 490671 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, p2143) 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-83552b8559f946d2a422eaf3e71069dd
Source dataset
uspto-grants-2009_05
Patent number
US07528159B2

Reaction notes

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