Hydrochloric Acid → HCID 13079712, compound

Participants

Reaction Steps

In 50 ml. of methanol there was dissolved 5 g. of 4-benzyloxy-3-nitro-α-[N-benzyl-N-{3-(3,4-dimethoxyphenyl)-1-methylpropyl}aminomethyl]benzyl alcohol and after adding to the solution 2.5 g. of iron powder and 5 ml. of 2N hydrochloric acid, the mixture was refluxed for 50 minutes. After cooling the reaction mixture, the insoluble materials were filtered off, and 5 ml. of a 2N potassium hydride methanol solution and 20 ml. of ethyl acetate were added to the filtrate. The insoluble materials were filtered off and the filtrate was concentrated under a reduced pressure. The residue was extracted with benzene, and the extract was washed with water, dried over anhydrous magnesium sulfate and concentrated under a reduced pressure to provide a yellowish brown viscous product. The product thus obtained was dissolved in benzene and after adding n-hexane until the solution became slightly muddy, the solution was allowed to stand whereby 2.7 g. of yellowish brown crystals of 3-amino-4-benzyloxy-α-[N-benzyl-N-{3-(3,4-dimethoxyphenyl)-1-methylpropyl}aminomethyl] benzyl alcohol [A]were obtained. The product was recrystallized from a mixture of benzene and n-hexane and was characterized by a melting point of 115° C.

Provenance & Evidence