Hydrochloric Acid → N-(4-nitrophenethyl)-1,2,3,4-tetrahydro-6,7-dimethoxyisoquinoline hydrochloride

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Reaction Steps

N-(4-Nitrophenylacetyl)-1,2,3,4-tetrahydro-6,7-dimethoxyisoquinoline (28.45 g, 0.08 m) was added portionwise to a stirred solution of 1 M borane in tetrahydrofuran (320 ml, 0.32 m) which was diluted with 180 ml of dry tetrahydrofuran and maintained under nitrogen. The mixture was heated to reflux for 3 hours, then cooled in an ice bath and carefully treated with 100 ml of 20% HCl. The mixture was heated to reflux for 1 hour, then allowed to cool. The solvent was removed at an aspirator (40°) and the residue slurried with cold water (400 ml) and the solid collected by filtration, washed with water and air dried. The hydrochloride salt was prepared in 300 ml of a methanol, isopropanol, ether mixture and dried to give 18.0 g N-(4-nitrophenethyl)-1,2,3,4-tetrahydro-6,7-dimethoxyisoquinoline hydrochloride, m.p. 154°-155°.

Provenance & Evidence