Sodium Iodide → 4-(2-iodoethyl)morpholine

HRID 1829014Notes

Reaction equation

HRID 1829014 reaction equation
Cl.Cl[CH2:3][CH2:4][N:5]1[CH2:10][CH2:9][O:8][CH2:7][CH2:6]1.[I-:11].[Na+]>CC(C)=O>[I:11][CH2:3][CH2:4][N:5]1[CH2:10][CH2:9][O:8][CH2:7][CH2:6]1

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 77210Morpholine, 4-(2-chloroethyl)-, hydrochloride (1:1)

Product 1

HCID 111491684-(2-iodoethyl)morpholineYield 59.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 4-(2-chloro-ethyl)-morpholine hydrochloride (5 g, 26.9 mmole), and sodium iodide (20 g, 134.4 mmole) in acetone (50 ml) was refluxed for 16 hours. After cooled to room temperature, the reaction was partitioned between CHCl3 and brine. The aqueous layer was extracted with CHCl3 (2×25 ml). The combined organic layers were washed with brine, and dried over anhydrous Mg2SO4. Removal of the solvent gave 4-(2-iodo-ethyl)-morpholine as a pale yellowish oil (3.84 g, 59%).

Workup

  1. temperaturewas refluxed for 16 hours
  2. customthe reaction was partitioned between CHCl3 and brine
  3. extractionThe aqueous layer was extracted with CHCl3 (2×25 ml)
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over anhydrous Mg2SO4
  6. customRemoval of the solvent

Sources & evidence

ORD record
ord-b5803652a742460cb752f359e2b504d5
Source dataset
uspto-grants-2006_06
Patent number
US07060844B2

Reaction notes

Loading…