Diisopropylamine → 3-(4-Chlorophenyl)prop-2-yn-1-amine

HRID 597872Notes

Reaction equation

HRID 597872 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5](I)=[CH:4][CH:3]=1.[CH2:9]([NH2:12])[C:10]#[CH:11].C(NC(C)C)(C)C>C(Cl)Cl.CCOC(C)=O.[Cu]I.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>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:11]#[C:10][CH2:9][NH2:12])=[CH:4][CH:3]=1

Participants

8

Reactant 3

HCID 7912DiisopropylamineHCID 125101-Chloro-4-iodobenzeneHCID 239041Propargylamine

Product 1

HCID 589523443-(4-Chlorophenyl)prop-2-yn-1-amine

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-chloro iodobenzene (25 g) in 400 mL CH2Cl2 at room temperature was added propargyl amine (13.5 mL), diisopropyl amine (37 mL), CuI (4 g) and Pd(PPh3)2Cl2 (3.7 g). The mixture was stirred overnight at room temperature, diluted with 600 mL EtOAc and filtered through a CELITE pad to remove insoluble materials. The solution washed with water, brine, dried over MgSO4, concentrated and purified by chromatography to provide 14.1 g of 3-(4-chloro-phenyl)-prop-2-ynylamine. MS: m/e 166.1 (MH+)

Workup

  1. filtrationfiltered through a CELITE pad
  2. customto remove insoluble materials
  3. washThe solution washed with water, brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. custompurified by chromatography

Sources & evidence

ORD record
ord-efc44ef22a6745ec93de5fb19b92ad4c
Source dataset
uspto-grants-2011_03
Patent number
US07897601B2

Reaction notes

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