Water → HCID 11173025, compound

HRID 1009666Notes

Reaction equation

HRID 1009666 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-0c08815a560e494da6ee2cda1c56cf9e
Source dataset
uspto-grants-2011_07
Patent number
US07973069B2

Reaction notes

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