N-(4-Bromophenyl)-2-chloroacetamide → N-(4-bromophenyl)-2-(pyrrolidin-1-yl)acetamide

HRID 1971551Notes

Reaction equation

HRID 1971551 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:12])[CH2:10]Cl)=[CH:4][CH:3]=1.[NH:13]1[CH2:17][CH2:16][CH2:15][CH2:14]1>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:12])[CH2:10][N:13]2[CH2:17][CH2:16][CH2:15][CH2:14]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 17374N-(4-Bromophenyl)-2-chloroacetamideHCID 31268Pyrrolidine

Product 1

HCID 1091709N-(4-bromophenyl)-2-(pyrrolidin-1-yl)acetamide

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

N-(4-Bromo-phenyl)-2-chloro-acetamide (0.3 g, 1.21 mmol) was dissolved in anhydrous toluene (10 ml). Pyrrolidine (0.3 ml, 3.63 mmol) was added dropwise to the mixture, which was then heated to reflux and stirred overnight. The toluene was removed under reduced pressure and the residue was dissolved in ethyl acetate. Saturated ammonium chloride was added and the aqueous layer was extracted twice with ethyl acetate. The organics were combined, washed with brine, dried over anhydrous magnesium sulfate and concentrated in vacuo. Yield 0.22 g, 65%. LCMS method: 2, RT: 2.62 min; MI: 283-285 [M+1].

Workup

  1. temperaturewas then heated
  2. temperatureto reflux
  3. customThe toluene was removed under reduced pressure
  4. dissolutionthe residue was dissolved in ethyl acetate
  5. additionSaturated ammonium chloride was added
  6. extractionthe aqueous layer was extracted twice with ethyl acetate
  7. washwashed with brine
  8. dry with materialdried over anhydrous magnesium sulfate
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2c80ca0214f74018ab7965bd44d4cd1b
Source dataset
uspto-grants-2013_04
Patent number
US08431596B2

Reaction notes

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