Acetaldehyde, 2,2-dimethoxy- → 3,4-Dihydro-6-(2,2-dimethoxyethyl)amino-4-(2-dimethylaminoethyl)-2H-1,4-benzoxazine

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Reaction Steps

6-Amino-3,4-dihydro-4-(2-dimethylaminoethyl)-2H-1,4-benzoxazine (D3, 1.78 g, 8.1 mmol) and dimethoxyacetaldehyde (40% in MTBE, 3.1 g) were hydrogenated over 10% palladium on carbon (0.5g) in ethanol (70 ml) for 24 h. The catalyst was filtered off, and the filtrate was evaporated to dryness. The residue was dissolved in ethyl acetate, washed with water and brine, dried (Na2SO4) and evaporated to give the title compound (1.92 g, 77%) as a brown oil.

Provenance & Evidence