Water → HCID 11367272, compound

HRID 1464912Notes

Reaction equation

HRID 1464912 reaction equation
I[C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][CH:8]=1)[NH2:5].[CH3:9][C:10]([CH3:14])([CH3:13])[C:11]#[CH:12].O>C(N(CC)CC)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu]I>[CH3:9][C:10]([CH3:14])([CH3:13])[C:11]#[C:12][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][CH:8]=1)[NH2:5]

Participants

7

Reactant 3

HCID 962WaterHCID 122713-IodoanilineHCID 135123,3-Dimethyl-1-butyne

Product 1

HCID 11367272HCID 11367272, compound

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 8471TriethylamineSolvent

Conditions

Temperature
20 °C

Procedure

1.05 g (1.5 mmol) of bis(triphenylphosphine)palladium(II) chloride and 0.26 g (1.5 mmol) of copper(I) iodide are added to a solution consisting of 5.47 g (25 mmol) of 3-iodoaniline in 40 ml of triethylamine. With ice-cooling, 3.08 g (37.5 mmol) of 3,3-dimethyl-1-butyne are added dropwise such that the temperature remains at 20° C. After the addition has ended, the mixture is stirred at 20° C. for 20 hours. The reaction solution is concentrated under reduced pressure and the residue formed is stirred into 1 l of water. The mixture is then extracted three times with diethyl ether. The combined organic phases are once more washed with water, dried with sodium sulphate and concentrated under reduced pressure. The crude product obtained is purified by silica gel chromatography (mobile phase methylene chloride). This gives 2.70 g (60% of theory) of 3-(3,3-dimethylbut-1-yn-1-yl)aniline having a content of 97% according to HPLC. log P=2.71.

Workup

  1. temperatureWith ice-cooling
  2. customremains at 20° C
  3. additionAfter the addition
  4. concentrationThe reaction solution is concentrated under reduced pressure
  5. customthe residue formed
  6. extractionThe mixture is then extracted three times with diethyl ether
  7. washThe combined organic phases are once more washed with water
  8. dry with materialdried with sodium sulphate
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-28c2722fe6c3444897517512ec8b3cf4
Source dataset
uspto-grants-2015_04
Patent number
US08999956B2

Reaction notes

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