4-Methylbenzylamine → 2,2-Dimethoxy-N-[(4-methylphenyl)methyl]acetamide

Participants

Reaction Conditions

Reaction Steps

A mixture of methyl dimethoxyacetate (1.35 g, 9.96 mmol) and 4-methylbenzylamine (1.21 g, 9.98 mmol) in a sealable tube was heated in a microwave reactor to 140° C. for 50 min. The reaction mixture was diluted with EtOAc (≈60 mL), washed with diluted aq. HCl, water, sat. NaHCO3 solution, and brine, and dried over MgSO4. The EtOAc extract was filtered, concentrated, and dried in vacuo overnight to give the title compound as pale yellow oil. It was used for the next step without further purification. 1H NMR (400 MHz, CDCl3): δ=7.20-7.13 (AA′BB′, 4H), 6.82 (brs, 1H), 4.75 (s, 1H), 4.44 (d, J=5.6 Hz, 2H), 3.40 (s, 6H), 2.34 (s, 3H). MS(ES+): m/z=246.10 (43) [MNa+], 224.11 (91) [MH+], 192.14 (8) [MH+-MeOH], 160.06 (80) [MH+-2 MeOH]. HPLC: tR=2.84 min (polar—5 min, ZQ3).

Provenance & Evidence