Trimethylsilylacetylene → N-(1-{4-[(trimethylsilyl)ethynyl]phenyl}ethyl)cyclopropylamine

HRID 1519697Notes

Reaction equation

HRID 1519697 reaction equation
[C:1]([Si:3]([CH3:6])([CH3:5])[CH3:4])#[CH:2].I[C:8]1[CH:13]=[CH:12][C:11]([CH:14]([NH:16][CH:17]2[CH2:19][CH2:18]2)[CH3:15])=[CH:10][CH:9]=1>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.C(Cl)(Cl)Cl>[CH3:4][Si:3]([C:1]#[C:2][C:8]1[CH:13]=[CH:12][C:11]([CH:14]([NH:16][CH:17]2[CH2:19][CH2:18]2)[CH3:15])=[CH:10][CH:9]=1)([CH3:6])[CH3:5]

Participants

6

Reactant 2

HCID 66111TrimethylsilylacetyleneHCID 43754631N-[1-(4-iodophenyl)ethyl]cyclopropanamine

Product 1

HCID 71268174N-(1-{4-[(trimethylsilyl)ethynyl]phenyl}ethyl)cyclopropylamineYield 67.9%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalyst2×HCID 6212ChloroformSolvent

Procedure

Ethynyl(trimethyl)silane (80 mg), PdCl2(PPh3)2 (29 mg), CuI (16 mg), and TEA (0.25 g) were added to a chloroform (5.0 mL) solution of N-[1-(4-iodophenyl)ethyl]cyclopropylamine (0.23 g) as obtained in Example 14-(1), and the mixture was stirred in a nitrogen atmosphere for 24 hours at room temperature. Further, stirring was continued for 2 hours at 45° C., and then PdCl2(PPh3)2 (29 mg) was added. After the system was refluxed in a nitrogen atmosphere for 5 hours, the reaction mixture was concentrated. The resulting residue was purified by OH type silica gel chromatography (hexane/ethyl acetate=85/15) to obtain N-(1-{4-[(trimethylsilyl)ethynyl]phenyl}ethyl)cyclopropylamine (brown oil) (0.14 g, 66%).

Workup

  1. stirringFurther, stirring
  2. waitwas continued for 2 hours at 45° C.
  3. temperatureAfter the system was refluxed in a nitrogen atmosphere for 5 hours
  4. concentrationthe reaction mixture was concentrated
  5. customThe resulting residue was purified by OH type silica gel chromatography (hexane/ethyl acetate=85/15)

Sources & evidence

ORD record
ord-1696dfc1fb904c238ce7b179c9498e8e
Source dataset
uspto-grants-2015_07
Patent number
US09073821B2

Reaction notes

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