Triethylsilane → HCID 29078034, compound

HRID 2095428Notes

Reaction equation

HRID 2095428 reaction equation
[C:1]1([CH2:7][C:8]([O:10][CH2:11][CH2:12][CH:13]2[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]2)=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[SiH](CC)(CC)CC>C1(C)C=CC=CC=1>[C:1]1([CH2:7][CH2:8][O:10][CH2:11][CH2:12][CH:13]2[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 12052TriethylsilaneHCID 56829485HCID 56829485, compound

Product 1

HCID 29078034HCID 29078034, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

In a oven-dried flask, 4-[2-(phenylacetoxy)ethyl]piperidine (101 mg, 0.41 mmol) and InBr3 (290 mg, 0.82 mmol, 2 equiv.) were dissolved in toluene (2 mL). After degassing and replacement of the atmosphere with Ar, Et3SiH (260 μL, 1.64 mmol, 4 equiv.) was added. The mixture was stirred at 90° C. for 4 h. After cooling to room temperature, the reaction was quenched with 1N HCl. After the aqueous layer was washed with EtOAc, its pH was raised to 9-10. After extraction with CH2Cl2, the organic layer was dried with Na2SO4. The solvent was removed to afford 4-[2-(2-phenylethoxy)ethyl]piperidine (40 mg, 42%) as a colorless oil.

Workup

  1. customAfter degassing
  2. temperatureAfter cooling to room temperature
  3. customthe reaction was quenched with 1N HCl
  4. washAfter the aqueous layer was washed with EtOAc, its pH
  5. temperaturewas raised to 9-10
  6. extractionAfter extraction with CH2Cl2
  7. dry with materialthe organic layer was dried with Na2SO4
  8. customThe solvent was removed

Sources & evidence

ORD record
ord-8c2f5be0cdb943a7bb53578d629bc707
Source dataset
uspto-grants-2013_05
Patent number
US08445684B2

Reaction notes

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