Hydrochloric Acid → 1-(p-Fluoroanilinomethyl)-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline hydrochloride

Participants

Reaction Steps

A mixture of 1-(N-benzyloxycarbonyl-p-fluoroanilinomethyl)-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline hydrochloride (4.6 g), conc. hydrochloric acid (46 ml) and acetic acid (46 ml) was refluxed for 2 hours. The reaction mixture was concentrated to dryness and the residue was dissolved in water and washed with a mixture of ether and ethyl acetate (1:1). The aqueous layer was treated with activated charcoal and concentrated to dryness to give 1-(p-fluoroanilinomethyl)-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline hydrochloride (3.1 g). The product (2.5 g) was converted into its d-camphor-10-sulfonate in a conventional manner and the crystals obtained were recrystallized from water to give the d-camphor-10-sulfonate of the above-mentioned product, mp 213° to 215° C.

Provenance & Evidence