1-Phenethylamine → 2,2-Dimethoxy-N-(1-phenylethyl)acetamide

Participants

Reaction Conditions

Reaction Steps

A mixture of methyl dimethoxyacetate (2.10 g, 15.6 mmol) and α-methylbenzylamine (1.90 g, 15.7 mmol) was stirred at ambient temperature for 5 d and at 40° C. for 4 d. To the reaction mixture was added hexane (5 mL), and the mixture was sonicated. Two layers formed, but no solid precipitated, even upon cooling, and the hexane layer was withdrawn with a pipette. This was repeated twice. The residue was dissolved in EtOAc (≈100 mL), and the solution was washed with aqueous solutions of NH4Cl, NaHCO3, and brine, and dried over MgSO4. The solution was filtered and dried in vacuo overnight to give the title compound as pale yellow oil. 1H NMR (CDCl3, 400 MHz): δ=7.38-7.30 (m, 4H), 7.29-7.24 (m, 1H), 6.80 (brs, 1H), 5.16 (dq, J=8.0, 6.8 Hz, 1H), 4.70 (s, 1H), 3.42 (s, 3H), 3.36 (s, 3H), 1.52 (d, J=6.8 Hz, 3H). MS(ES+): m/z=246.07 (64) [MNa+], 224.11 (78) [MH+], 192.11 (52) [MH+-MeOH], 160.10 (60) [MH+-2 MeOH]. HPLC: tR=2.76 min (polar—5 min, ZQ3).

Provenance & Evidence