4-Iodophenol → 1-(2-(4-Iodophenoxy)ethyl)pyrrolidine

HRID 1916754Notes

Reaction equation

HRID 1916754 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.Cl.Cl[CH2:11][CH2:12][N:13]1[CH2:17][CH2:16][CH2:15][CH2:14]1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[I:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:11][CH2:12][N:13]2[CH2:17][CH2:16][CH2:15][CH2:14]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 108944-IodophenolHCID 11430Potassium CarbonateHCID 816681-(2-Chloroethyl)pyrrolidine hydrochloride

Product 1

HCID 219591661-(2-(4-Iodophenoxy)ethyl)pyrrolidine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A reaction mixture of 44 g (0.2 mol) 4-iodophenol, 34 g (0.2 mol) 1-(2-chloro-ethyl)-pyrrolidine-hydrochloride, 110.56 g (0.8 mol) K2CO3 and 800 mL DMF is stirred for 48 h at RT. The reaction mixture is filtered and the filtrate is evaporated down. The residue is taken up in water and extracted with EtOAc. The organic phase is extracted with saturated NaCl solution and dried over Na2SO4. The purification is carried out by column chromatography on silica gel (EtOAc/MeOH/NH3 85:15:1.5).

Workup

  1. filtrationThe reaction mixture is filtered
  2. customthe filtrate is evaporated down
  3. extractionextracted with EtOAc
  4. extractionThe organic phase is extracted with saturated NaCl solution
  5. dry with materialdried over Na2SO4
  6. customThe purification

Sources & evidence

ORD record
ord-a51743834413470dbc11f85107daf55e
Source dataset
uspto-grants-2013_12
Patent number
US08618132B2

Reaction notes

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