Benzoyl chloride → N-[4-(1-benzoyl-4-piperidinyl)butyl]-3-(3-pyridinyl)-2-propenamide

HRID 1294460Notes

Reaction equation

HRID 1294460 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])[CH:22]=[CH:23][C:24]2[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=2)[CH2:12][CH2:11]1.[OH-].[Na+]>ClCCl>[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])[CH:22]=[CH: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 14798Sodium HydroxideHCID 57260083N-[4-(piperidin-4-yl)-butyl]-3-(pyridin-3-yl)-acrylamide

Product 1

HCID 53396328N-[4-(1-benzoyl-4-piperidinyl)butyl]-3-(3-pyridinyl)-2-propenamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

5.1 g (36.2 mMol) benzoyl chloride are dissolved in 150 ml abs. dichlormethane and cooled to ca 0° C. under moisture exclusion. 10.4 g (36.2 mmol) N-[4-(piperidin-4-yl)-butyl]-3-(pyridin-3-yl)-acrylamide (substance 14) are dissolved in 50 ml abs. dichlormethane and added dropwise under ice cooling. The mixture is stirred overnight at RT without further cooling. Subsequently, the suspension is added to 60 ml 2 M sodium hydroxide and extracted twice, each with 80 ml dichlormethane. The combined organic phases are washed twice, each with 60 ml water, dried over sodium sulfate and the solvent is removed under vacuum. The residue is chromatographically purified over silica gel with CHCl3/CH3OH (97/3 to 95/5) and recrystalized from 75 ml acetonitrile. Colorless crystals with a MP of 100–102° C. are recovered; yield: 9.8 g (69%).

Workup

  1. extractionextracted twice
  2. washThe combined organic phases are washed twice
  3. dry with materialeach with 60 ml water, dried over sodium sulfate
  4. customthe solvent is removed under vacuum
  5. customThe residue is chromatographically purified over silica gel with CHCl3/CH3OH (97/3 to 95/5)
  6. customrecrystalized from 75 ml acetonitrile
  7. customColorless crystals with a MP of 100–102° C. are recovered

Sources & evidence

ORD record
ord-423f61be7b924c04a115691ddc297b64
Source dataset
uspto-grants-2007_07
Patent number
US07241745B2

Reaction notes

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