Phenylacetaldehyde → HCID 69593417, compound

Participants

Reaction Steps

Trifluoroacetic acid (0.38 mL, 4.99 mmol) in CH2Cl2 (0.38 mL) was added dropwise to a 0° C. stirring solution of 101 (0.115 g, 0.318 mmol) in CH2Cl2 (0.40 mL). When the reaction was judged complete by TLC, the solvent and excess trifluoroacetic acid were removed in vacuo. The crude residue was dissolved in DMF (1.54 mL, 0.18M), then phenylacetaldehyde (0.10 mL, 0.832 mmol), acetic acid (0.078 mL), and Na(OAc)3BH (0.118 g, 0.555 mmol) were added sequentially. When the reaction was judged complete by TLC, saturated aqueous K2CO3 was added. The organic layer was removed, and 5% aqueous HCl was added. The organic layer was discarded, and the aqueous layer was basified with saturated aqueous NH4OH. The organic layer was removed, dried with Na2SO4, and concentrated in vacuo. Purification by silica gel chromatography (99:1::CH2Cl2:2N NH3 in EtOH) provided (1-benzylpiperidine-3-ylethyl)-N-phenylpropionamide (103). 1H NMR (CDCl3): 7.46–7.24 (8H, m), 7.15 (2H, broad d, J=7.8 Hz), 3.72 (2H, J=7.8 Hz), 3.52 (1H, J=13.2 Hz), 3.45 (1H, d, J=13.2 Hz), 2.79 (2H, broad d, J=8.2 Hz), 2.03 (2H, q, J=7.3 Hz), 1.91 (1H, td, J=11.0, 3.3 Hz), 1.84–1.30 (7H, m), 1.05 (3H, t, J=7.4 Hz), 0.98–0.84 (1H, m) ppm. 13C NMR (CDCl3): 173.65, 142.93, 138.4, 129.83, 129.35, 128.52, 128.31, 127.95, 127.07 63.68, 60.21, 54.22, 47.34, 34.14, 32.51, 30.84, 28.04, 25.34, 9.78 ppm. LRMS: 350.95.

Provenance & Evidence