Iodine → 1-(4-iodophenyl)pyrrolidine

HRID 2421344Notes

Reaction equation

HRID 2421344 reaction equation
[I:1]I.[C:3]1([N:9]2[CH2:13][CH2:12][CH2:11][CH2:10]2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C(=O)(O)[O-].[Na+].S([O-])([O-])(=O)=S.[Na+].[Na+]>O.C(O)C>[I:1][C:6]1[CH:7]=[CH:8][C:3]([N:9]2[CH2:13][CH2:12][CH2:11][CH2:10]2)=[CH:4][CH:5]=1

Participants

7

Reactant 4

HCID 807IodineHCID 24477Sodium ThiosulfateHCID 777261-PhenylpyrrolidineHCID 516892Sodium Bicarbonate

Product 1

HCID 112773071-(4-iodophenyl)pyrrolidineYield 19.6%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Iodine (6.09 g) was added slowly to a stirred solution of phenylpyrrolidine (3.21 g) and sodium bicarbonate (2.75 g) in water (30 ml). The reaction was stirred for 1 h and then left to stand overnight. The solid was isolated by filtration, dissolved in ethanol (50 ml) and discoloured with aqueous sodium thiosulfate. The product was then isolated by filtration and recrystalised from ethanol to give the desired product as a brown/red powder (1.17 g).

Workup

  1. waitleft
  2. waitto stand overnight
  3. customThe solid was isolated by filtration
  4. customThe product was then isolated by filtration
  5. customrecrystalised from ethanol

Sources & evidence

ORD record
ord-2f45c5cf34784633aa5c9259f45eadde
Source dataset
uspto-grants-2011_06
Patent number
US07956084B2

Reaction notes

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