Piperidine → 1-(4-Trimethylsilanylethynylbenzyl)pyrrolidine

HRID 735004Notes

Reaction equation

HRID 735004 reaction equation
I[C:2]1[CH:13]=[CH:12][C:5]([CH2:6][N:7]2[CH2:11][CH2:10][CH2:9][CH2:8]2)=[CH:4][CH:3]=1.N1CCCCC1.[CH3:20][Si:21]([C:24]#[CH:25])([CH3:23])[CH3:22]>[Cu]I>[CH3:20][Si:21]([C:24]#[C:25][C:2]1[CH:13]=[CH:12][C:5]([CH2:6][N:7]2[CH2:11][CH2:10][CH2:9][CH2:8]2)=[CH:4][CH:3]=1)([CH3:23])[CH3:22]

Participants

5

Reactant 3

HCID 8082PiperidineHCID 66111TrimethylsilylacetyleneHCID 185258671-(4-Iodobenzyl)pyrrolidine

Product 1

HCID 688167401-(4-Trimethylsilanylethynylbenzyl)pyrrolidine

Reagents, catalysts & solvents 1

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

Conditions

Temperature
0 °C

Procedure

A reaction mixture of 1 g (3.48 mmol) of 1-(4-iodobenzyl)pyrrolidine, 5 mL of piperidine, 105 mg (0.091 mmol) of tetrakistriphenylphosphine palladium, and 10 mg (0.053 mmol) of copper (I) iodide is cooled to 0° C. At this temperature, 0.59 mL (4.18 mmol) of trimethylsilylacetylene is added dropwise and then the cooling bath is removed. It is stirred for 3 hours at ambient temperature, then combined with a saturated aqueous ammonium chloride solution, and extracted with dichloromethane. The organic phase is dried over sodium sulfate. The purification is carried out by column chromatography on silica gel (eluant: cyclohexane/ethyl acetate (1:1)). Yield: 0.75 g (83.6% of theory); C16H23NSi (M=257.45); calc.: molecular ion peak (M+H)+: 258; found: molecular ion peak (M+H)+: 258.

Workup

  1. customthe cooling bath is removed
  2. extractionextracted with dichloromethane
  3. dry with materialThe organic phase is dried over sodium sulfate
  4. customThe purification

Sources & evidence

ORD record
ord-ce67a05fc9e848069826b7a802e34465
Source dataset
uspto-grants-2009_09
Patent number
US07592373B2

Reaction notes

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