Piperidine → HCID 22241280, compound

HRID 892215Notes

Reaction equation

HRID 892215 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][O:7][C:8]1[CH:9]=[C:10](I)[CH:11]=[CH:12][CH:13]=1.N1CCCCC1.[CH3:21][Si:22]([C:25]#[CH:26])([CH3:24])[CH3:23]>C1COCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][O:7][C:8]1[CH:9]=[C:10]([C:26]#[C:25][Si:22]([CH3:24])([CH3:23])[CH3:21])[CH:11]=[CH:12][CH:13]=1

Participants

6

Reactant 3

HCID 8082PiperidineHCID 66111TrimethylsilylacetyleneHCID 22241268HCID 22241268, compound

Product 1

HCID 22241280HCID 22241280, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

3-(2-Methoxy-ethoxymethoxy)-phenyliodide (12.1 g, 39 mmol, 96) and tetrakis(triphenylphosphine)palladium (1.2 g, 1.0 mmol) and cuprous iodide (0.096 g, 0.5 mmol) are dissolved in THF (120 mL) and to this is added piperidine (12 mL) and (trimethylsilyl)acetylene (8 mL, 57 mmol). This mixture is degassed and is then stirred for 2 hours. The reaction is then diluted with ether and washed twice with water and brine and the organic layer dried over magnesium sulfate. The solvent is removed in vacuo to give the title compound. MS (EI) 206 (M)+.

Workup

  1. customThis mixture is degassed
  2. additionThe reaction is then diluted with ether
  3. washwashed twice with water and brine
  4. dry with materialthe organic layer dried over magnesium sulfate
  5. customThe solvent is removed in vacuo

Sources & evidence

ORD record
ord-045ad18d9e0d4b9ca385b219afcdf440
Source dataset
uspto-grants-2006_02
Patent number
US07005440B1

Reaction notes

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