Propargyl bromide → HCID 57168291, compound

HRID 567770Notes

Reaction equation

HRID 567770 reaction equation
[CH2:1](Br)[C:2]#[CH:3].I[C:6]1[CH:12]=[CH:11][C:9]([NH2:10])=[CH:8][CH:7]=1>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cu]I.N1CCCCC1>[NH:10]1[CH2:9][CH2:8][CH2:3][CH:2]([C:6]2[CH:12]=[CH:11][C:9]([NH:10][CH2:12][C:6]#[CH:7])=[CH:8][CH:7]=2)[CH2:1]1

Participants

6

Reactant 2

HCID 7842Propargyl bromideHCID 108934-Iodoaniline

Product 1

HCID 57168291HCID 57168291, compoundYield 15%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418397HCID 178418397, compoundCatalystHCID 8082PiperidineSolvent

Conditions

Temperature
0 °C

Procedure

Under nitrogen gas, to a pre-cooled (0° C., ice-bath) flask containing 400 mL piperidine, a number of reagents were added, including 14.2 mL of propargyl bromide (80 wt. % solution in toluene, 127 mmol), 22.0 g of 4-iodoaniline (100 mmol), 1.4 g of tetrakis(triphenylphosphine)palladium O) (1.2 mmol) and 200 mg copper(I) iodide (1.05 mmol). The mixture was heated for 18 h (40-45° C., oil bath temperature). The reaction mixture was filtered through Celite and the solvent (piperidine) was removed. The crude solid was redissolved with 125 mL AcOEt. The acetate solution was extracted with water (2×450 mL) and dried with brine (2×250 mL). Flash column chromatography on aluminum oxide (Brockmann I, basic, Aldrich #19,944-3, CH2Cl2) supplied 4-(3-piperidinyl)-propargyl-aniline as a light yellow solid (3.1 g; yield: 15%).

Workup

  1. additiona number of reagents were added
  2. temperatureThe mixture was heated for 18 h (40-45° C., oil bath temperature)
  3. filtrationThe reaction mixture was filtered through Celite
  4. customthe solvent (piperidine) was removed
  5. dissolutionThe crude solid was redissolved with 125 mL AcOEt
  6. extractionThe acetate solution was extracted with water (2×450 mL)
  7. dry with materialdried with brine (2×250 mL)

Sources & evidence

ORD record
ord-96c7eaac12424bf89aa1f5bcf6e233f8
Source dataset
uspto-grants-2001_01
Patent number
US06180640B2

Reaction notes

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