Water → HCID 11173025, compound

HRID 506134Notes

Reaction equation

HRID 506134 reaction equation
[I:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.C([O-])([O-])=O.[Cs+].[Cs+].[CH:15](I)([CH3:17])[CH3:16].O>CN(C=O)C>[I:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][CH:15]([CH3:17])[CH3:16])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6362Isopropyl iodideHCID 10796Cesium carbonateHCID 108934-Iodoaniline

Product 1

HCID 11173025HCID 11173025, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 4-iodoaniline (4.38 g, 20.0 mmol), Cs2CO3 (16.3 g, 50.0 mmol), isopropyliodide (3.0 mL, 30.0 mmol) in DMF (20 mL) was stirred in a sealed tube at 70° C. for 24 h. The mixture was cooled to room temperature and poured into water (200 mL). The organic layer was separated and washed with water and brine and purified on silica gel (CH2Cl2/hexanes, 1:1) to provide (4-iodophenyl)-isopropylamine (3.26 g, 63%).

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. customThe organic layer was separated
  3. washwashed with water and brine
  4. custompurified on silica gel (CH2Cl2/hexanes, 1:1)

Sources & evidence

ORD record
ord-840962a8bcb3490f8ef4ccc5364d9ee2
Source dataset
uspto-grants-2010_08
Patent number
US07781478B2

Reaction notes

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