6-Propylpyridin-2-amine → Piperidine-1-sulfonic acid (6-propyl-pyridin-2-yl)-amide

HRID 1454807Notes

Reaction equation

HRID 1454807 reaction equation
[CH2:1]([C:4]1[N:9]=[C:8]([NH2:10])[CH:7]=[CH:6][CH:5]=1)[CH2:2][CH3:3].[N:11]1([S:17](Cl)(=[O:19])=[O:18])[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1>N1C=CC=CC=1.CCOC(C)=O>[CH2:1]([C:4]1[N:9]=[C:8]([NH:10][S:17]([N:11]2[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)(=[O:19])=[O:18])[CH:7]=[CH:6][CH:5]=1)[CH2:2][CH3:3]

Participants

5

Reactant 2

HCID 30163096-Propylpyridin-2-amineHCID 11298344Piperidine-1-sulfonyl chloride

Product 1

HCID 11608902Piperidine-1-sulfonic acid (6-propyl-pyridin-2-yl)-amideYield 32%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 6-propyl-pyridin-2-ylamine (0.2 g) and piperidine-1-sulfonyl chloride (0.296 g, Bull. Soc. Chim. Fr.; 1936, 2143) in pyridine (7 mL) was heated to reflux for 15 h. After concentration of the reaction mixture 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 the desired piperidine-1-sulfonic acid (6-propyl-pyridin-2-yl)-amide (0.133 g) as a colorless amorphous solid. MS (ESI−): 282.0 ([M−H]−).

Workup

  1. temperatureto reflux for 15 h
  2. washwhich was then washed with 1N aqueous HCl, saturated brine
  3. dry with materialdried over sodium sulphate
  4. concentrationconcentrated in vacuo
  5. concentrationCombination of the purified fractions and concentration in vacuo

Sources & evidence

ORD record
ord-4aeeebc56fa845c2beda3018efbb0773
Source dataset
uspto-grants-2009_01
Patent number
US07482341B2

Reaction notes

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