Benzoyl chloride → N-[4-(1-Benzoylpiperidin-4-YL)butyl]-3-pyridin-3-ylpropanamide

HRID 1178404Notes

Reaction equation

HRID 1178404 reaction equation
[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH:10]1[CH2:15][CH2:14][CH:13]([CH2:16][CH2:17][CH2:18][CH2:19][NH:20][C:21](=[O:30])[CH2:22][CH2:23][C:24]2[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=2)[CH2:12][CH2:11]1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[C:1]([N:10]1[CH2:15][CH2:14][CH:13]([CH2:16][CH2:17][CH2:18][CH2:19][NH:20][C:21](=[O:30])[CH2:22][CH2:23][C:24]2[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=2)[CH2:12][CH2:11]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 11430Potassium CarbonateHCID 18425707N-(4-piperidin-4-yl-butyl)-3-(pyridin-3-yl)-propionamide

Product 1

HCID 9543513N-[4-(1-Benzoylpiperidin-4-YL)butyl]-3-pyridin-3-ylpropanamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3.48 ml (30 mmol) benzoyl chloride, 8.7 g (30 mmol) N-(4-piperidin-4-yl-butyl)-3-(pyridin-3-yl)-propionamide and 16.6 g (120 mmol) potassium carbonate are stirred in 160 ml DMF at RT overnight. Subsequently, this is filtered and the filtrate is concentrated under vacuum to a large extent. The residue is taken up in 400 ml CHCl3 and washed twice, each with 100 ml water. The organic phase is dried over sodium sulfate and the solvent is removed under vacuum. The residue is chromatographically purified over silica gel with CHCl3/CH3OH (95/5) and precipitates as an amorphous solid after drawing off the solvent.

Workup

  1. filtrationSubsequently, this is filtered
  2. concentrationthe filtrate is concentrated under vacuum to a large extent
  3. washwashed twice
  4. dry with materialThe organic phase is dried over sodium sulfate
  5. customthe solvent is removed under vacuum
  6. customThe residue is chromatographically purified over silica gel with CHCl3/CH3OH (95/5)
  7. customprecipitates as an amorphous solid

Sources & evidence

ORD record
ord-a11497185fba4a8a922d29ae36bac0af
Source dataset
uspto-grants-2007_10
Patent number
US07276524B2

Reaction notes

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