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

HRID 1971553Notes

Reaction equation

HRID 1971553 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-9824ee289ecc4ad7bb12d803b71ed7bc
Source dataset
uspto-grants-2013_04
Patent number
US08431596B2

Reaction notes

Loading…