Propyne → 4-(Prop-1-yn-1-yl)aniline

HRID 734990Notes

Reaction equation

HRID 734990 reaction equation
I[C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.N1CC[CH2:12][CH2:11][CH2:10]1.C#CC>[Cu]I.O>[C:10]([C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1)#[C:11][CH3:12]

Participants

6

Reactant 3

HCID 6335PropyneHCID 8082PiperidineHCID 108934-Iodoaniline

Product 1

HCID 450791534-(Prop-1-yn-1-yl)aniline

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 962WaterSolvent

Procedure

5.47 g (25 mmol) of 4-iodoaniline, 0.878 g (1.25 mmol) of bis-triphenylphosphine palladium dichloride, 0.47 g (2.5 mmol) of copper (I) iodide, and 20 mL of piperidine are placed in a pressure apparatus. Then 6.1 bar gaseous propyne are piped into the pressure apparatus, while the temperature rises to 39° C. It is therefore cooled with water. The mixture is stirred for 2 hours at ambient temperature and the reaction mixture is then extracted with ethyl acetate and water. The organic phase is dried over sodium sulfate, evaporated down, and the residue purified by column chromatography on silica gel (eluant: cyclohexane/ethyl acetate (4:1)). Yield: 2.1 g (64% of theory); C9H9N (M=131.17); calc.: molecular ion peak (M+H)+: 132; found: molecular ion peak (M+H)+: 132.

Workup

  1. customrises to 39° C
  2. extractionthe reaction mixture is then extracted with ethyl acetate and water
  3. dry with materialThe organic phase is dried over sodium sulfate
  4. customevaporated down
  5. customthe residue purified by column chromatography on silica gel (eluant: cyclohexane/ethyl acetate (4:1))

Sources & evidence

ORD record
ord-a2068621436141e9b50f77a25d47218f
Source dataset
uspto-grants-2009_09
Patent number
US07592373B2

Reaction notes

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