Hydrochloric Acid → 1-(2-(4-Iodophenoxy)ethyl)pyrrolidine

HRID 1916520Notes

Reaction equation

HRID 1916520 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.Cl[CH2:10][CH2:11][N:12]1[CH2:16][CH2:15][CH2:14][CH2:13]1.Cl.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[I:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:10][CH2:11][N:12]2[CH2:16][CH2:15][CH2:14][CH2:13]2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 108944-IodophenolHCID 11430Potassium CarbonateHCID 816691-(2-Chloroethyl)pyrrolidine

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A suspension of 22 g (100 mmol) 4-iodophenol, 17 g (100 mmol) 1-(2-chloro-ethyl)-pyrrolidine (used as the hydrochloride) and 55.3 g (400 mmol) K2CO3 in 400 mL DMF is stirred for 48 h at RT. The solvent is evaporated down i.vac., the residue is combined with water, the aqueous phase exhaustively extracted with EtOAc, the combined organic phases are washed with saturated, aqueous NaCl solution and dried over Na2SO4. After the desiccant and solvent have been eliminated the residue is purified on silica gel (EtOAc/MeOH/NH3 85:15:1.5).

Workup

  1. customThe solvent is evaporated down i.vac
  2. extractionthe aqueous phase exhaustively extracted with EtOAc
  3. washthe combined organic phases are washed with saturated, aqueous NaCl solution
  4. dry with materialdried over Na2SO4
  5. customis purified on silica gel (EtOAc/MeOH/NH3 85:15:1.5)

Sources & evidence

ORD record
ord-97bbf2ee7669494abce2ae55c7745643
Source dataset
uspto-grants-2013_12
Patent number
US08618132B2

Reaction notes

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