Hydrochloric Acid → N1-[3-amino-4-(methyloxy)phenyl]-N1,N2,N2-trimethylglycinamide

Participants

Reaction Steps

A solution of 1,1-dimethylethyl [5-[(N,N-dimethylglycyl)(methyl)amino]-2-(methyloxy)phenyl]carbamate (2.01 g, 5.96 mmol) in 1,4-dioxane (40 ml) was treated with 4.0M HCl in dioxanes (7.45 ml, 29.8 mmol) and stirred for 3 hours. Additional 4.0M HCl in dioxanes (7.45 ml, 29.8 mmol) was added and the reaction was stirred for 16 hours. The solution was poured into ethyl acetate, diluted with water, and neutralized by careful addition of solid potassium carbonate. The aqueous layer was washed with chloroform and the organic layers were combined, dried over sodium sulfate, filtered, and taken to a residue under reduced pressure to afford N1-[3-amino-4-(methyloxy)phenyl]-N1,N2,N2-trimethylglycinamide (1.19 g, 5.01 mmol, 84% yield) as a tan oil. 1H NMR (400 MHz, DMSO-d6) δ ppm 6.78 (d, J=8.2 Hz, 1 H), 6.48 (d, J=2.4 Hz, 1 H), 6.41 (d, J=8.2 Hz, 1 H), 4.91 (br. s., 2 H), 3.77 (s, 3 H), 3.05 (s, 3 H), 2.82 (s, 2 H), 2.12 (s, 6 H).

Provenance & Evidence