Iodine → 1-(4-iodophenyl)pyrrolidine

HRID 1245824Notes

Reaction equation

HRID 1245824 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 (506 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-4a856bbcb0a24b48b7195cb5abccb470
Source dataset
uspto-grants-2006_10
Patent number
US07125896B2

Reaction notes

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