Sodium Bicarbonate → 1-(N-benzyloxycarbonyl-p-benzyloxyanilinomethyl)-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline

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Reaction Steps

To 1-(N-benzyloxycarbonyl-p-benzyloxyanilinomethyl)-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline p-toluenesulfonate (10.0 g) was added a saturated sodium bicarbonate aqueous solution and then the mixture was extracted with ethyl acetate. The extract was washed with water, dried and the solvent was distilled off to give 1-(N-benzyloxycarbonyl-p-benzyloxyanilinomethyl)-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline (8.2 g). To this residue (8.2 g) were added conc. hydrochloric acid (50 ml) and ethanol (50 ml) and the mixture was refluxed for 4 hours with stirring. The reaction mixture was concentrated to dryness under reduced pressure and the residue was pulverized with ether to give a powder of 1-(p-hydroxyanilinomethyl)-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline dihydrochloride (5.8 g), mp 170° to 184° C. (dec).

Provenance & Evidence