Oxalic Acid → HCID 70430491, compound

Participants

Reaction Steps

4-(4-Aminosulphonylphenyl)butanone-2 was reacted with (S)-(-)-α-phenylethylamine and p-toluenesulphonic acid as the catalyst in toluene with separation of water to give the Schiff's base (S)-N-(α-methylbenzyl)-1-methyl-3-(4-aminosulphonylphenyl)propylimine. The imine was hydrogenated in methanol in the presence of Raney-nickel to give a mixture of the optical isomers of N-(α-methylbenzyl)-1-methyl-3-(4-aminosulphonylphenyl)propylamine. The amine was converted with oxalic acid into a mixture of the oxalates from which there was obtained by two-fold crystallization pure (S)-1-methyl-3-(4-aminosulphonylphenyl)propylamine oxalate of melting point 123°-127°, [α]D20 =-68° (c=1.0 in methanol). Hydrogenolysis of this substance in alcohol under 4 bar of hydrogen at 60° for 24 hours yielded pure (S)-1-methyl-3-(4-aminosulphonylphenyl)propylamine.

Provenance & Evidence