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

HRID 1472816Notes

Reaction equation

HRID 1472816 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-4cdc35ea5fe5468ab2d352aa1b6fe650
Source dataset
uspto-grants-2015_04
Patent number
US09012633B2

Reaction notes

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