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

HRID 1383909Notes

Reaction equation

HRID 1383909 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-180ace20d3a8494a91addc1c17a3aa01
Source dataset
uspto-grants-2001_07
Patent number
US06255496B1

Reaction notes

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