Piperidine → 1-[2-(4-Trimethylsilanylethynyl-phenoxy)-ethyl]-pyrrolidine

HRID 1916755Notes

Reaction equation

HRID 1916755 reaction equation
I[C:2]1[CH:15]=[CH:14][C:5]([O:6][CH2:7][CH2:8][N:9]2[CH2:13][CH2:12][CH2:11][CH2:10]2)=[CH:4][CH:3]=1.[C:16]([Si:18]([CH3:21])([CH3:20])[CH3:19])#[CH:17].N1CCCCC1>[Cu]I>[CH3:19][Si:18]([C:16]#[C:17][C:2]1[CH:15]=[CH:14][C:5]([O:6][CH2:7][CH2:8][N:9]2[CH2:13][CH2:12][CH2:11][CH2:10]2)=[CH:4][CH:3]=1)([CH3:21])[CH3:20]

Participants

5

Reactant 3

HCID 8082PiperidineHCID 66111TrimethylsilylacetyleneHCID 219591661-(2-(4-Iodophenoxy)ethyl)pyrrolidine

Product 1

HCID 673634551-[2-(4-Trimethylsilanylethynyl-phenoxy)-ethyl]-pyrrolidine

Reagents, catalysts & solvents 1

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)Catalyst

Procedure

Under a nitrogen atmosphere and while cooling with ice a reaction mixture of 1.5 g (4.72 mmol) 1-[2-(4-iodo-phenoxy)-ethyl]-pyrrolidine, 0.735 ml (5.2 mmol) ethynyl-trimethyl-silane, 15 mL piperidine, 115.5 mg (0.1 mmol) tetrakis-triphenylphosphane-palladium and 19 mg (0.1 mmol) CuI is stirred for 1 h. Then the reaction mixture is evaporated down, the residue is taken up in 20 mL water and extracted with EtOAc. The organic phase is dried over Na2SO4. The purification is carried out by column chromatography on silica gel (EtOAc/MeOH/NH3 95:5:0.5).

Workup

  1. temperatureUnder a nitrogen atmosphere and while cooling with ice
  2. customThen the reaction mixture is evaporated down
  3. extractionextracted with EtOAc
  4. dry with materialThe organic phase is dried over Na2SO4
  5. customThe purification

Sources & evidence

ORD record
ord-0de9a844d51c4d5eaf0ee3bf9f794ecd
Source dataset
uspto-grants-2013_12
Patent number
US08618132B2

Reaction notes

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