Thionyl Chloride → HCID 70217041, compound

Participants

Reaction Steps

Equimolar amounts of methyl (R,S)-2-bromo-2-phenylacetate and 3-hydroxymethylaniline are reacted to give methyl N-(3-hydroxymethylphenyl)aminophenyl-acetate. By reaction with thionyl chloride to give methyl N-(3-chloromethylphenyl)aminophenylacetate and subsequent reaction with sodium azide, methyl N-(3-azidomethylphenyl)aminophenylacetate (“A”) is obtained. A solution of 9.2 g of “A” in 350 ml of ethyl acetate is hydrogenated for 35 minutes in the presence of 1 g of Pd/C (5%). After removing the catalyst and the solvent, methyl N-(3-aminomethylphenyl)aminophenyl-acetate) (“B”) is obtained as an oil, RT 19.5; FAB 271.

Provenance & Evidence