Triethylamine → 2-Pent-1-ynylaniline

HRID 1095370Notes

Reaction equation

HRID 1095370 reaction equation
I[C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[NH2:4].[CH:9]#[C:10][CH2:11][CH2:12][CH3:13].C(N(CC)CC)C>C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl.[Cu](I)I.C(#N)C>[C:9]([C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[NH2:4])#[C:10][CH2:11][CH2:12][CH3:13]

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 119952-IodoanilineHCID 123091-Pentyne

Product 1

HCID 109317192-Pent-1-ynylanilineYield 68.9%

Reagents, catalysts & solvents 3

HCID 83717Copper iodideCatalystHCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 6342AcetonitrileSolvent

Procedure

A mixture of 2-iodoaniline (500 mg, 2.28 mmol), 1-pentyne (0.27 mL, 2.74 mmol), bis(triphenylphosphine)palladium (II) chloride (77 mg, 0.11 mmol), copper iodide (21 mg, 0.11 mmol), triethylamine (0.95 mL, 6.84 mmol), and acetonitrile (10 mL) was stirred at ambient temperature for 2 hours. The reaction mixture was concentrated under reduced pressure. The residue was stirred in diethyl ether and filtered. The filtrate was concentrated under reduced pressure to afford 0.25 g of 2-pent-1-ynylaniline.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. stirringThe residue was stirred in diethyl ether
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-361d42370f1847658f301723761415e6
Source dataset
uspto-grants-2012_03
Patent number
US08138173B2

Reaction notes

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