Pyrrolidine → N-(4-bromophenyl)-3-pyrrolidin-1-ylpropanamide

HRID 1054366Notes

Reaction equation

HRID 1054366 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:12])[CH:10]=[CH2:11])=[CH:4][CH:3]=1.[NH:13]1[CH2:17][CH2:16][CH2:15][CH2:14]1>C(O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9](=[O:12])[CH2:10][CH2:11][N:13]2[CH2:17][CH2:16][CH2:15][CH2:14]2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 31268PyrrolidineHCID 263609n-(4-Bromophenyl)prop-2-enamide

Product 1

HCID 739898N-(4-bromophenyl)-3-pyrrolidin-1-ylpropanamide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

N-(4-Bromo-phenyl)-acrylamide (0.3 g, 1.33 mmol) was dissolved in ethanol. Pyrrolidine (0.12 ml, 1.46 mmol) was added and the mixture was heated to reflux overnight. The solvent was removed under reduced pressure and the residue was dissolved in ethyl acetate. Aqueous ammonium chloride was added and the aqueous layer was extracted twice with ethyl acetate. The organics were combined, dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo to yield the desired product. Yield 0.24 g, 60%. LCMS method: 2, RT: 2.67 min; MI: 297-299 [M+1].

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux overnight
  3. customThe solvent was removed under reduced pressure
  4. dissolutionthe residue was dissolved in ethyl acetate
  5. additionAqueous ammonium chloride was added
  6. extractionthe aqueous layer was extracted twice with ethyl acetate
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-33cc4cdc4a5b49d783460679f303907f
Source dataset
uspto-grants-2016_07
Patent number
US09394301B2

Reaction notes

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