Triethylsilane → HCID 23722966, compound

Participants

Reaction Conditions

Reaction Steps

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).

Provenance & Evidence