tert-Butyl methyl ether → N-[3-(2-dimethylaminoethoxy)4-methoxyphenyl]aminoacetaldehyde dimethyl acetal

Participants

Reaction Steps

A solution of 3-(2-dimethylaminoethoxy)-4-methoxyaniline (D14, 5.7 g, 0.027 mole) in ethanol (120 ml) was treated with a solution of 2,2-dimethoxyacetaldehyde in methyl tert-butyl ether (9.5 g of approx. 40% solution, 0.036 mole) and kept at room temperature for 16 hours. The solution was then hydrogenated over 10% Pd-C (0.6 g) at atmospheric pressure and temperature for 7 hours. The catalyst was removed by filtration through kieselguhr and the filtrate concentrated in vacuo. The residue was dissolved in ethyl acetate (100 ml), washed twice with water (2×60 ml), then dried (Na2SO4) and concentrated in vacuo. The residue was chromatographed on silica gel eluting with 5% methanol/chloroform to afford the title compound as a red oil (5.4 g, 67%).

Provenance & Evidence