Sodium Iodide → N-2-[4-Iodophenoxy]ethyldodecylamine

HRID 1700890Notes

Reaction equation

HRID 1700890 reaction equation
[CH2:1]([NH2:13])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].C(N(C(C)C)CC)(C)C.[I-].[Na+].Br[CH2:26][CH2:27][O:28][C:29]1[CH:34]=[CH:33][C:32]([I:35])=[CH:31][CH:30]=1>C(O)(C)C>[I:35][C:32]1[CH:33]=[CH:34][C:29]([O:28][CH2:27][CH2:26][NH:13][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])=[CH:30][CH:31]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 13583DodecylamineHCID 81531DiisopropylethylamineHCID 19058471-(2-Bromoethoxy)-4-iodobenzene

Product 1

HCID 18319005N-2-[4-Iodophenoxy]ethyldodecylamineYield 82%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of dodecylamine (30 g, 162 mmol), diisopropylethylamine (22 ml, 128 mmol), sodium iodide (1.3 g, 8.5 mmol), 1-[2-bromoethoxy]-4-iodobenzene (13.9 g, 42.5 mmol) and isopropanol (250 ml) was stirred and refluxed for 24 h. After cooling to r.t., the mixture was filtered, washed with dichloromethane and concentrated in vacuo . The residue was chromatographed on silica gel (dichloromethane/methanol 50:1 to 20:1) to afford the title compound (15 g, 82%) as a white solid.

Workup

  1. temperaturerefluxed for 24 h
  2. filtrationthe mixture was filtered
  3. washwashed with dichloromethane
  4. concentrationconcentrated in vacuo
  5. customThe residue was chromatographed on silica gel (dichloromethane/methanol 50:1 to 20:1)

Sources & evidence

ORD record
ord-f4d7d09e7d0f4fc2bd558c8de9ddec29
Source dataset
uspto-grants-2002_02
Patent number
US06350892B1

Reaction notes

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