Allyl bromide → 1-Allyl-2-(4-bromo-phenyl)-pyrrolidine

HRID 2236513Notes

Reaction equation

HRID 2236513 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:12][CH2:11][CH2:10][NH:9]2)=[CH:4][CH:3]=1.[CH2:13](Br)[CH:14]=[CH2:15].C([O-])([O-])=O.[K+].[K+]>C1COCC1>[CH2:15]([N:9]1[CH2:10][CH2:11][CH2:12][CH:8]1[C:5]1[CH:4]=[CH:3][C:2]([Br:1])=[CH:7][CH:6]=1)[CH:14]=[CH2:13]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 42814942-(4-Bromophenyl)pyrrolidine

Product 1

HCID 513585141-Allyl-2-(4-bromo-phenyl)-pyrrolidineYield 62.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

2-(4-Bromo-phenyl)-pyrrolidine (640 mg, 2.83 mmol) and allyl bromide (343 mg, 2.83 mmol) is mixed in THF (15 mL) and K2CO3 (390 mg, 2.83 mmol) is then added. The mixture is heated at reflux for 2 h before THF is removed under reduced pressure and the residue is partitioned between EtOAc and H2O. The EtOAc layer is dried and concentrated and the residue is then subjected to chromatography to provide the desired product (470 mg, 62.4%).

Workup

  1. temperatureThe mixture is heated
  2. customis removed under reduced pressure
  3. customthe residue is partitioned between EtOAc and H2O
  4. dry with materialThe EtOAc layer is dried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-05acbbb59d8f41cfad2f78684b922a54
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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