Methylamine → N-Methyltyramine

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Reaction Steps

To 250 mg of 4-hydroxyphenethyl bromide in a round-bottomed flask, a 10 M excess of MeNH2 (6.2 mL of 2M in MeOH) was added and the solution was stirred at r.t. overnight. After filtration, the solvent was removed to give a brown oil in 80% yield. TLC (EtAc:MeOH, 9:1 v/v): RF=0.33. 1H NMR, δ: 9.42 (s, 1H), 7.10 (d, 2H), 6.75 (d, 2H), 3.60 (s, 3H), 2.84 (t, 2H), 2.60 (t, 2H), 1.90 (s, 1H). 13C NMR, δ: 167.5, 131.2, 128.3, 112.4, 41.5, 36.4, 35.0. Anal. calcd for C9H13NO: C, 71.49; H, 8.67; N, 9.26%. Found; C, 71.50; H, 8.80; N, 9.20%.

Provenance & Evidence