Triethylsilane → HCID 23722966, compound

HRID 2095419Notes

Reaction equation

HRID 2095419 reaction equation
[C:1]1([CH2:7][C:8]([O:10][CH2:11][CH:12]2[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]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][CH:12]2[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 12052TriethylsilaneHCID 53410149HCID 53410149, compound

Product 1

HCID 23722966HCID 23722966, compoundYield 59.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

In a oven-dried flask, 4-[(phenylacetoxy)methyl]piperidine (53 mg, 0.23 mmol) and InBr3 (161 mg, 0.46 mmol) were dissolved in toluene (1.5 mL). After degassing and replacement of the atmosphere with Ar, Et3SiH (145 μL, 0.91 mmol, 4.0 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. The aqueous layer was washed with EtOAc, and its pH was raised to 9-10. After extraction with CH2Cl2, the organic layer was dried with Na2SO4. The solvent was removed to furnish 4-[(2-phenylethoxy)methyl]piperidine (30 mg, 59%) as a colorless oil. 1H NMR (CDCl3, 400 MHz) δ 7.22 (m, 5H), 3.61 (t, 2H, J=7.2 Hz), 3.26 (d, 2H, J=6.0 Hz), 3.07 (d, 2H, J=12.0 Hz), 2.87 (t, 2H, J=7.2 Hz), 2.59 (t, 2H, J=11.6 Hz), 2.31 (br, 1H), 1.70 (m, 3H), 1.09 (m, 2H).

Workup

  1. customAfter degassing
  2. temperatureAfter cooling to room temperature
  3. customthe reaction was quenched with 1N HCl
  4. washThe aqueous layer was washed with EtOAc, and 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-eeb30f22005a443487a28c9712fe8c71
Source dataset
uspto-grants-2013_05
Patent number
US08445684B2

Reaction notes

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