2-Pyrrolidone → 1-(4-Iodobenzyl)pyrrolidin-2-one

HRID 76155Notes

Reaction equation

HRID 76155 reaction equation
[NH:1]1[CH2:5][CH2:4][CH2:3][C:2]1=[O:6].[H-].[Na+].[I:9][C:10]1[CH:17]=[CH:16][C:13]([CH2:14]Br)=[CH:12][CH:11]=1>CN(C=O)C>[I:9][C:10]1[CH:17]=[CH:16][C:13]([CH2:14][N:1]2[CH2:5][CH2:4][CH2:3][C:2]2=[O:6])=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 120252-PyrrolidoneHCID 24758Sodium hydrideHCID 9542584-Iodobenzyl bromide

Product 1

HCID 509928621-(4-Iodobenzyl)pyrrolidin-2-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 140 μl (1.68 mmol) 2-pyrrolidone in 5 mL DMF are added 110 mg (2.53 mmol) sodium hydride. Then 500 mg (1.68 mmol) 4-iodobenzyl bromide are added by several portions and the resulting mixture is stirred at r.t. over night. The solvent is removed in vacuo and the residue is resolved in DCM and water. The layers are separated and the organic layer is dried with Na2SO4, filtrated and the solvent is removed in vacuo. The crude product is purified by HPLC.

Workup

  1. customThe solvent is removed in vacuo
  2. customThe layers are separated
  3. dry with materialthe organic layer is dried with Na2SO4
  4. filtrationfiltrated
  5. customthe solvent is removed in vacuo
  6. customThe crude product is purified by HPLC

Sources & evidence

ORD record
ord-392c23370f18485ea0366c42b5d658a8
Source dataset
uspto-grants-2014_09
Patent number
US08835472B2

Reaction notes

Loading…